The crystal structure of chlorido{
-2-[(2-oxidobenzylidene)amino]ethanolato-
4O,
N,
O':
O'}{2-[(2-oxidobenzylidene)amino]ethanolato-
3O,
N,
O'}trivinylditin(IV), [Sn
2(C
2H
3)
3(C
9H
9NO
2)
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 Sn
IV atom.
Supporting information
CCDC references: 964524; 964525
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 = 680.31 | Dx = 1.722 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5961 reflections |
a = 12.5649 (3) Å | θ = 2.6–27.3° |
b = 15.9508 (4) Å | µ = 2.04 mm−1 |
c = 13.3525 (3) Å | T = 273 K |
β = 101.335 (1)° | Prism, pale yellow |
V = 2623.91 (10) Å3 | 0.26 × 0.24 × 0.13 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6341 independent reflections |
Radiation source: sealed tube | 4378 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 28.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.620, Tmax = 0.778 | k = −19→21 |
23707 measured reflections | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-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 parameters | Δρmax = 0.71 e Å−3 |
12 restraints | Δρmin = −0.60 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Sn1 | 0.30253 (2) | 0.516017 (17) | 0.11957 (2) | 0.04689 (9) | |
O1 | 0.2873 (2) | 0.39519 (16) | 0.1888 (2) | 0.0522 (7) | |
O2 | 0.3305 (3) | 0.60157 (19) | 0.0070 (3) | 0.0739 (10) | |
N1 | 0.3438 (3) | 0.4264 (2) | 0.0118 (3) | 0.0519 (9) | |
C1 | 0.2915 (4) | 0.3243 (3) | 0.1236 (3) | 0.0665 (14) | |
H1A | 0.2200 | 0.3134 | 0.0828 | 0.080* | |
H1B | 0.3148 | 0.2749 | 0.1644 | 0.080* | |
C2 | 0.3690 (4) | 0.3429 (3) | 0.0560 (3) | 0.0615 (12) | |
H2A | 0.4428 | 0.3416 | 0.0950 | 0.074* | |
H2B | 0.3624 | 0.3012 | 0.0022 | 0.074* | |
C3 | 0.3305 (3) | 0.4368 (3) | −0.0858 (3) | 0.0512 (10) | |
H3 | 0.3357 | 0.3889 | −0.1244 | 0.061* | |
C4 | 0.3087 (4) | 0.5130 (3) | −0.1409 (3) | 0.0500 (10) | |
C5 | 0.3132 (4) | 0.5918 (3) | −0.0925 (4) | 0.0568 (11) | |
C6 | 0.3022 (4) | 0.6621 (3) | −0.1555 (5) | 0.0762 (16) | |
H6 | 0.3089 | 0.7151 | −0.1259 | 0.091* | |
C7 | 0.2819 (4) | 0.6556 (4) | −0.2600 (5) | 0.0800 (16) | |
H7 | 0.2735 | 0.7040 | −0.2995 | 0.096* | |
C8 | 0.2737 (4) | 0.5779 (4) | −0.3077 (4) | 0.0709 (14) | |
H8 | 0.2581 | 0.5736 | −0.3785 | 0.085* | |
C9 | 0.2892 (4) | 0.5083 (3) | −0.2478 (3) | 0.0601 (12) | |
H9 | 0.2868 | 0.4559 | −0.2788 | 0.072* | |
C10 | 0.1359 (4) | 0.5412 (3) | 0.0955 (4) | 0.0659 (13) | |
H10 | 0.0917 | 0.4974 | 0.1086 | 0.079* | |
C11A | 0.092 (2) | 0.6041 (14) | 0.0676 (16) | 0.092 (6) | 0.40 |
H11A | 0.0640 | 0.6123 | −0.0015 | 0.110* | 0.40 |
H11B | 0.0851 | 0.6459 | 0.1145 | 0.110* | 0.40 |
C11B | 0.0829 (12) | 0.5926 (9) | 0.0223 (10) | 0.085 (4) | 0.60 |
H11C | 0.0601 | 0.6451 | 0.0396 | 0.102* | 0.60 |
H11D | 0.0692 | 0.5754 | −0.0456 | 0.102* | 0.60 |
C12 | 0.4311 (4) | 0.5658 (3) | 0.2269 (4) | 0.0606 (12) | |
H12 | 0.4591 | 0.5343 | 0.2847 | 0.073* | |
C13 | 0.4739 (5) | 0.6393 (4) | 0.2161 (5) | 0.0883 (18) | |
H13A | 0.4472 | 0.6718 | 0.1588 | 0.106* | |
H13B | 0.5310 | 0.6590 | 0.2656 | 0.106* | |
Sn2 | 0.28086 (2) | 0.374990 (17) | 0.34778 (2) | 0.03992 (8) | |
Cl1 | 0.25599 (10) | 0.37708 (7) | 0.52536 (8) | 0.0566 (3) | |
O3 | 0.2459 (2) | 0.25149 (17) | 0.3247 (2) | 0.0548 (7) | |
O4 | 0.2547 (2) | 0.50265 (16) | 0.3312 (2) | 0.0450 (7) | |
N2 | 0.1008 (3) | 0.3760 (2) | 0.3038 (3) | 0.0506 (9) | |
C14 | 0.1372 (4) | 0.2300 (3) | 0.3237 (4) | 0.0746 (15) | |
H14A | 0.1262 | 0.2257 | 0.3934 | 0.089* | |
H14B | 0.1220 | 0.1756 | 0.2916 | 0.089* | |
C15 | 0.0596 (4) | 0.2939 (3) | 0.2670 (4) | 0.0724 (14) | |
H15A | 0.0564 | 0.2893 | 0.1940 | 0.087* | |
H15B | −0.0127 | 0.2853 | 0.2804 | 0.087* | |
C16 | 0.0388 (3) | 0.4335 (3) | 0.3252 (3) | 0.0546 (11) | |
H16 | −0.0349 | 0.4213 | 0.3157 | 0.066* | |
C17 | 0.0724 (3) | 0.5148 (3) | 0.3624 (3) | 0.0457 (10) | |
C18 | 0.1782 (3) | 0.5462 (3) | 0.3641 (3) | 0.0444 (9) | |
C19 | 0.2028 (4) | 0.6273 (3) | 0.3991 (4) | 0.0579 (12) | |
H19 | 0.2709 | 0.6497 | 0.3982 | 0.070* | |
C20 | 0.1266 (5) | 0.6749 (3) | 0.4352 (4) | 0.0713 (14) | |
H20 | 0.1449 | 0.7285 | 0.4600 | 0.086* | |
C21 | 0.0240 (5) | 0.6445 (3) | 0.4351 (4) | 0.0718 (15) | |
H21 | −0.0265 | 0.6772 | 0.4597 | 0.086* | |
C22 | −0.0027 (4) | 0.5658 (3) | 0.3984 (3) | 0.0593 (12) | |
H22 | −0.0723 | 0.5456 | 0.3972 | 0.071* | |
C23 | 0.4523 (4) | 0.3710 (3) | 0.3806 (4) | 0.0700 (14) | |
H23 | 0.4915 | 0.3416 | 0.3399 | 0.084* | |
C24A | 0.5041 (15) | 0.4161 (11) | 0.4687 (14) | 0.103 (6) | 0.45 |
H24A | 0.5496 | 0.3882 | 0.5216 | 0.124* | 0.45 |
H24B | 0.4924 | 0.4734 | 0.4734 | 0.124* | 0.45 |
C24B | 0.5121 (11) | 0.3584 (9) | 0.4588 (12) | 0.095 (4) | 0.55 |
H24C | 0.5333 | 0.4024 | 0.5042 | 0.114* | 0.55 |
H24D | 0.5382 | 0.3046 | 0.4753 | 0.114* | 0.55 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.0608 (2) | 0.03569 (16) | 0.04775 (17) | −0.00116 (13) | 0.01928 (13) | −0.00800 (12) |
O1 | 0.080 (2) | 0.0393 (16) | 0.0408 (15) | 0.0020 (14) | 0.0216 (14) | −0.0036 (12) |
O2 | 0.125 (3) | 0.0411 (18) | 0.066 (2) | −0.0052 (18) | 0.042 (2) | −0.0045 (15) |
N1 | 0.080 (3) | 0.0367 (19) | 0.044 (2) | 0.0037 (17) | 0.0252 (18) | −0.0057 (15) |
C1 | 0.112 (4) | 0.042 (3) | 0.048 (3) | 0.001 (3) | 0.023 (3) | −0.010 (2) |
C2 | 0.093 (4) | 0.039 (2) | 0.059 (3) | 0.013 (2) | 0.031 (3) | −0.004 (2) |
C3 | 0.068 (3) | 0.042 (2) | 0.049 (2) | −0.002 (2) | 0.025 (2) | −0.0096 (19) |
C4 | 0.056 (3) | 0.050 (3) | 0.048 (2) | 0.001 (2) | 0.020 (2) | 0.000 (2) |
C5 | 0.069 (3) | 0.046 (3) | 0.062 (3) | 0.005 (2) | 0.029 (2) | 0.009 (2) |
C6 | 0.092 (4) | 0.049 (3) | 0.100 (4) | 0.006 (3) | 0.050 (3) | 0.008 (3) |
C7 | 0.078 (4) | 0.082 (4) | 0.088 (4) | 0.012 (3) | 0.035 (3) | 0.037 (3) |
C8 | 0.060 (3) | 0.098 (4) | 0.057 (3) | 0.005 (3) | 0.016 (2) | 0.019 (3) |
C9 | 0.062 (3) | 0.067 (3) | 0.053 (3) | −0.001 (2) | 0.015 (2) | 0.001 (2) |
C10 | 0.063 (3) | 0.062 (3) | 0.072 (3) | 0.008 (3) | 0.011 (3) | 0.002 (3) |
C11A | 0.101 (10) | 0.079 (9) | 0.091 (10) | 0.026 (7) | 0.012 (8) | −0.009 (8) |
C11B | 0.100 (7) | 0.067 (6) | 0.079 (7) | 0.008 (5) | −0.005 (6) | −0.008 (6) |
C12 | 0.056 (3) | 0.063 (3) | 0.066 (3) | −0.008 (2) | 0.020 (2) | −0.017 (2) |
C13 | 0.079 (4) | 0.078 (4) | 0.108 (5) | −0.027 (3) | 0.018 (3) | −0.016 (3) |
Sn2 | 0.04462 (16) | 0.03744 (15) | 0.03827 (14) | 0.00138 (12) | 0.00955 (11) | −0.00247 (11) |
Cl1 | 0.0726 (7) | 0.0593 (7) | 0.0401 (5) | 0.0077 (6) | 0.0167 (5) | −0.0007 (5) |
O3 | 0.070 (2) | 0.0382 (16) | 0.0558 (17) | −0.0031 (14) | 0.0124 (15) | −0.0050 (13) |
O4 | 0.0477 (16) | 0.0372 (15) | 0.0538 (17) | 0.0017 (12) | 0.0185 (13) | −0.0001 (12) |
N2 | 0.047 (2) | 0.047 (2) | 0.056 (2) | −0.0037 (17) | 0.0051 (16) | 0.0009 (16) |
C14 | 0.092 (4) | 0.049 (3) | 0.078 (4) | −0.016 (3) | 0.005 (3) | −0.004 (3) |
C15 | 0.065 (3) | 0.061 (3) | 0.085 (4) | −0.017 (3) | 0.000 (3) | −0.011 (3) |
C16 | 0.041 (2) | 0.063 (3) | 0.058 (3) | 0.000 (2) | 0.006 (2) | 0.014 (2) |
C17 | 0.049 (2) | 0.044 (2) | 0.048 (2) | 0.009 (2) | 0.0178 (19) | 0.0115 (18) |
C18 | 0.053 (2) | 0.041 (2) | 0.041 (2) | 0.0108 (19) | 0.0135 (18) | 0.0097 (17) |
C19 | 0.070 (3) | 0.040 (2) | 0.067 (3) | 0.006 (2) | 0.020 (2) | 0.006 (2) |
C20 | 0.099 (4) | 0.042 (3) | 0.078 (4) | 0.017 (3) | 0.029 (3) | 0.001 (2) |
C21 | 0.089 (4) | 0.061 (3) | 0.077 (3) | 0.037 (3) | 0.043 (3) | 0.022 (3) |
C22 | 0.057 (3) | 0.063 (3) | 0.064 (3) | 0.017 (2) | 0.027 (2) | 0.023 (2) |
C23 | 0.048 (3) | 0.080 (4) | 0.083 (4) | 0.016 (3) | 0.015 (3) | 0.012 (3) |
C24A | 0.087 (11) | 0.112 (14) | 0.088 (11) | 0.005 (12) | −0.040 (8) | −0.008 (12) |
C24B | 0.060 (7) | 0.117 (12) | 0.099 (10) | 0.005 (9) | −0.007 (6) | 0.010 (10) |
Geometric parameters (Å, º) top
Sn1—C12 | 2.093 (4) | C13—H13A | 0.9300 |
Sn1—C10 | 2.094 (5) | C13—H13B | 0.9300 |
Sn1—O2 | 2.110 (3) | Sn2—O3 | 2.029 (3) |
Sn1—O1 | 2.162 (3) | Sn2—O4 | 2.068 (3) |
Sn1—N1 | 2.163 (3) | Sn2—C23 | 2.113 (5) |
O1—C1 | 1.434 (5) | Sn2—N2 | 2.223 (3) |
Sn2—O1 | 2.164 (3) | Sn2—Cl1 | 2.4520 (10) |
O2—C5 | 1.313 (5) | O3—C14 | 1.405 (6) |
N1—C3 | 1.291 (5) | O4—C18 | 1.329 (4) |
N1—C2 | 1.466 (5) | N2—C16 | 1.271 (5) |
C1—C2 | 1.482 (6) | N2—C15 | 1.457 (5) |
C1—H1A | 0.9700 | C14—C15 | 1.508 (7) |
C1—H1B | 0.9700 | C14—H14A | 0.9700 |
C2—H2A | 0.9700 | C14—H14B | 0.9700 |
C2—H2B | 0.9700 | C15—H15A | 0.9700 |
C3—C4 | 1.419 (6) | C15—H15B | 0.9700 |
C3—H3 | 0.9300 | C16—C17 | 1.424 (6) |
C4—C9 | 1.403 (6) | C16—H16 | 0.9300 |
C4—C5 | 1.409 (6) | C17—C22 | 1.400 (6) |
C5—C6 | 1.393 (7) | C17—C18 | 1.416 (6) |
C6—C7 | 1.372 (7) | C18—C19 | 1.390 (6) |
C6—H6 | 0.9300 | C19—C20 | 1.380 (6) |
C7—C8 | 1.388 (8) | C19—H19 | 0.9300 |
C7—H7 | 0.9300 | C20—C21 | 1.376 (7) |
C8—C9 | 1.359 (7) | C20—H20 | 0.9300 |
C8—H8 | 0.9300 | C21—C22 | 1.365 (7) |
C9—H9 | 0.9300 | C21—H21 | 0.9300 |
C10—C11A | 1.17 (2) | C22—H22 | 0.9300 |
C10—C11B | 1.347 (14) | C23—C24B | 1.178 (14) |
C10—H10 | 0.9300 | C23—C24A | 1.422 (16) |
C11A—H11A | 0.9300 | C23—H23 | 0.9300 |
C11A—H11B | 0.9300 | C24A—H24A | 0.9300 |
C11B—H11C | 0.9300 | C24A—H24B | 0.9300 |
C11B—H11D | 0.9300 | C24B—H24C | 0.9300 |
C12—C13 | 1.311 (6) | C24B—H24D | 0.9300 |
C12—H12 | 0.9300 | | |
| | | |
C12—Sn1—C10 | 130.24 (18) | H13A—C13—H13B | 120.0 |
C12—Sn1—O2 | 91.61 (18) | O3—Sn2—O4 | 156.21 (12) |
C10—Sn1—O2 | 93.90 (18) | O3—Sn2—C23 | 100.61 (17) |
C12—Sn1—O1 | 99.59 (16) | O4—Sn2—C23 | 100.70 (16) |
C10—Sn1—O1 | 93.84 (17) | O3—Sn2—O1 | 92.55 (11) |
O2—Sn1—O1 | 157.24 (11) | O4—Sn2—O1 | 77.53 (10) |
C12—Sn1—N1 | 116.88 (15) | C23—Sn2—O1 | 88.56 (17) |
C10—Sn1—N1 | 112.86 (17) | O3—Sn2—N2 | 77.76 (12) |
O2—Sn1—N1 | 81.85 (12) | O4—Sn2—N2 | 80.37 (12) |
O1—Sn1—N1 | 75.42 (11) | C23—Sn2—N2 | 176.50 (18) |
C1—O1—Sn1 | 115.2 (2) | O1—Sn2—N2 | 88.42 (12) |
C1—O1—Sn2 | 119.4 (2) | O3—Sn2—Cl1 | 95.45 (8) |
Sn1—O1—Sn2 | 125.13 (12) | O4—Sn2—Cl1 | 92.43 (8) |
C5—O2—Sn1 | 128.8 (3) | C23—Sn2—Cl1 | 96.79 (16) |
C3—N1—C2 | 119.9 (3) | O1—Sn2—Cl1 | 169.39 (8) |
C3—N1—Sn1 | 125.9 (3) | N2—Sn2—Cl1 | 86.48 (10) |
C2—N1—Sn1 | 113.1 (2) | C14—O3—Sn2 | 114.8 (3) |
O1—C1—C2 | 108.6 (4) | C18—O4—Sn2 | 126.1 (2) |
O1—C1—H1A | 110.0 | C16—N2—C15 | 122.1 (4) |
C2—C1—H1A | 110.0 | C16—N2—Sn2 | 125.6 (3) |
O1—C1—H1B | 110.0 | C15—N2—Sn2 | 111.0 (3) |
C2—C1—H1B | 110.0 | O3—C14—C15 | 111.8 (4) |
H1A—C1—H1B | 108.4 | O3—C14—H14A | 109.3 |
N1—C2—C1 | 108.1 (4) | C15—C14—H14A | 109.3 |
N1—C2—H2A | 110.1 | O3—C14—H14B | 109.3 |
C1—C2—H2A | 110.1 | C15—C14—H14B | 109.3 |
N1—C2—H2B | 110.1 | H14A—C14—H14B | 107.9 |
C1—C2—H2B | 110.1 | N2—C15—C14 | 106.6 (4) |
H2A—C2—H2B | 108.4 | N2—C15—H15A | 110.4 |
N1—C3—C4 | 127.3 (4) | C14—C15—H15A | 110.4 |
N1—C3—H3 | 116.3 | N2—C15—H15B | 110.4 |
C4—C3—H3 | 116.3 | C14—C15—H15B | 110.4 |
C9—C4—C5 | 119.9 (4) | H15A—C15—H15B | 108.6 |
C9—C4—C3 | 117.3 (4) | N2—C16—C17 | 125.7 (4) |
C5—C4—C3 | 122.7 (4) | N2—C16—H16 | 117.2 |
O2—C5—C6 | 119.5 (5) | C17—C16—H16 | 117.2 |
O2—C5—C4 | 123.6 (4) | C22—C17—C18 | 118.9 (4) |
C6—C5—C4 | 116.8 (4) | C22—C17—C16 | 118.4 (4) |
C7—C6—C5 | 122.0 (5) | C18—C17—C16 | 122.7 (4) |
C7—C6—H6 | 119.0 | O4—C18—C19 | 118.1 (4) |
C5—C6—H6 | 119.0 | O4—C18—C17 | 123.2 (4) |
C6—C7—C8 | 121.1 (5) | C19—C18—C17 | 118.7 (4) |
C6—C7—H7 | 119.4 | C20—C19—C18 | 120.4 (5) |
C8—C7—H7 | 119.4 | C20—C19—H19 | 119.8 |
C9—C8—C7 | 118.0 (5) | C18—C19—H19 | 119.8 |
C9—C8—H8 | 121.0 | C21—C20—C19 | 121.3 (5) |
C7—C8—H8 | 121.0 | C21—C20—H20 | 119.3 |
C8—C9—C4 | 122.1 (5) | C19—C20—H20 | 119.3 |
C8—C9—H9 | 119.0 | C22—C21—C20 | 119.2 (4) |
C4—C9—H9 | 119.0 | C22—C21—H21 | 120.4 |
C11A—C10—Sn1 | 127.4 (13) | C20—C21—H21 | 120.4 |
C11B—C10—Sn1 | 124.4 (8) | C21—C22—C17 | 121.5 (4) |
C11A—C10—H10 | 116.3 | C21—C22—H22 | 119.2 |
C11B—C10—H10 | 111.4 | C17—C22—H22 | 119.2 |
Sn1—C10—H10 | 116.3 | C24B—C23—Sn2 | 129.5 (8) |
C10—C11A—H11A | 120.0 | C24A—C23—Sn2 | 116.0 (9) |
C10—C11A—H11B | 120.0 | C24B—C23—H23 | 96.5 |
H11A—C11A—H11B | 120.0 | C24A—C23—H23 | 122.0 |
C10—C11B—H11C | 120.0 | Sn2—C23—H23 | 122.0 |
C10—C11B—H11D | 120.0 | C23—C24A—H24A | 120.0 |
H11C—C11B—H11D | 120.0 | C23—C24A—H24B | 120.0 |
C13—C12—Sn1 | 122.8 (4) | H24A—C24A—H24B | 120.0 |
C13—C12—H12 | 118.6 | C23—C24B—H24C | 120.0 |
Sn1—C12—H12 | 118.6 | C23—C24B—H24D | 120.0 |
C12—C13—H13A | 120.0 | H24C—C24B—H24D | 120.0 |
C12—C13—H13B | 120.0 | | |
| | | |
C12—Sn1—O1—C1 | −126.3 (3) | C1—O1—Sn2—O4 | −171.5 (3) |
C10—Sn1—O1—C1 | 101.8 (3) | Sn1—O1—Sn2—O4 | 14.26 (16) |
O2—Sn1—O1—C1 | −7.8 (5) | C1—O1—Sn2—C23 | 87.2 (3) |
N1—Sn1—O1—C1 | −10.8 (3) | Sn1—O1—Sn2—C23 | −87.0 (2) |
C12—Sn1—O1—Sn2 | 48.1 (2) | C1—O1—Sn2—N2 | −91.0 (3) |
C10—Sn1—O1—Sn2 | −83.8 (2) | Sn1—O1—Sn2—N2 | 94.75 (18) |
O2—Sn1—O1—Sn2 | 166.6 (3) | C1—O1—Sn2—Cl1 | −152.3 (4) |
N1—Sn1—O1—Sn2 | 163.6 (2) | Sn1—O1—Sn2—Cl1 | 33.5 (6) |
C12—Sn1—O2—C5 | 149.6 (4) | O4—Sn2—O3—C14 | −40.6 (4) |
C10—Sn1—O2—C5 | −79.9 (4) | C23—Sn2—O3—C14 | 166.2 (3) |
O1—Sn1—O2—C5 | 29.7 (6) | O1—Sn2—O3—C14 | −104.8 (3) |
N1—Sn1—O2—C5 | 32.6 (4) | N2—Sn2—O3—C14 | −17.0 (3) |
C12—Sn1—N1—C3 | −115.1 (4) | Cl1—Sn2—O3—C14 | 68.2 (3) |
C10—Sn1—N1—C3 | 63.4 (4) | O3—Sn2—O4—C18 | 66.4 (4) |
O2—Sn1—N1—C3 | −27.4 (4) | C23—Sn2—O4—C18 | −140.4 (3) |
O1—Sn1—N1—C3 | 151.4 (4) | O1—Sn2—O4—C18 | 133.5 (3) |
C12—Sn1—N1—C2 | 76.9 (3) | N2—Sn2—O4—C18 | 43.0 (3) |
C10—Sn1—N1—C2 | −104.6 (3) | Cl1—Sn2—O4—C18 | −43.0 (3) |
O2—Sn1—N1—C2 | 164.6 (3) | O3—Sn2—N2—C16 | 157.5 (4) |
O1—Sn1—N1—C2 | −16.6 (3) | O4—Sn2—N2—C16 | −31.9 (4) |
Sn1—O1—C1—C2 | 35.5 (5) | O1—Sn2—N2—C16 | −109.5 (4) |
Sn2—O1—C1—C2 | −139.3 (3) | Cl1—Sn2—N2—C16 | 61.2 (4) |
C3—N1—C2—C1 | −128.6 (4) | O3—Sn2—N2—C15 | −9.6 (3) |
Sn1—N1—C2—C1 | 40.2 (5) | O4—Sn2—N2—C15 | 161.0 (3) |
O1—C1—C2—N1 | −48.1 (5) | O1—Sn2—N2—C15 | 83.3 (3) |
C2—N1—C3—C4 | −178.2 (4) | Cl1—Sn2—N2—C15 | −106.0 (3) |
Sn1—N1—C3—C4 | 14.5 (7) | Sn2—O3—C14—C15 | 41.0 (5) |
N1—C3—C4—C9 | −175.4 (4) | C16—N2—C15—C14 | −136.3 (5) |
N1—C3—C4—C5 | 8.9 (7) | Sn2—N2—C15—C14 | 31.3 (5) |
Sn1—O2—C5—C6 | 158.7 (3) | O3—C14—C15—N2 | −46.9 (6) |
Sn1—O2—C5—C4 | −23.7 (7) | C15—N2—C16—C17 | 179.3 (4) |
C9—C4—C5—O2 | 179.6 (4) | Sn2—N2—C16—C17 | 13.6 (6) |
C3—C4—C5—O2 | −4.7 (7) | N2—C16—C17—C22 | −169.4 (4) |
C9—C4—C5—C6 | −2.7 (7) | N2—C16—C17—C18 | 10.8 (7) |
C3—C4—C5—C6 | 172.9 (4) | Sn2—O4—C18—C19 | 145.0 (3) |
O2—C5—C6—C7 | −178.6 (5) | Sn2—O4—C18—C17 | −37.0 (5) |
C4—C5—C6—C7 | 3.6 (7) | C22—C17—C18—O4 | −179.6 (4) |
C5—C6—C7—C8 | −1.5 (8) | C16—C17—C18—O4 | 0.1 (6) |
C6—C7—C8—C9 | −1.7 (8) | C22—C17—C18—C19 | −1.6 (6) |
C7—C8—C9—C4 | 2.5 (7) | C16—C17—C18—C19 | 178.1 (4) |
C5—C4—C9—C8 | −0.3 (7) | O4—C18—C19—C20 | −179.3 (4) |
C3—C4—C9—C8 | −176.2 (4) | C17—C18—C19—C20 | 2.6 (6) |
C12—Sn1—C10—C11A | 65.9 (14) | C18—C19—C20—C21 | −1.7 (7) |
O2—Sn1—C10—C11A | −29.5 (13) | C19—C20—C21—C22 | −0.1 (8) |
O1—Sn1—C10—C11A | 171.9 (13) | C20—C21—C22—C17 | 1.1 (7) |
N1—Sn1—C10—C11A | −112.3 (13) | C18—C17—C22—C21 | −0.2 (6) |
C12—Sn1—C10—C11B | 99.8 (8) | C16—C17—C22—C21 | −180.0 (4) |
O2—Sn1—C10—C11B | 4.3 (8) | O3—Sn2—C23—C24B | −85.0 (11) |
O1—Sn1—C10—C11B | −154.2 (8) | O4—Sn2—C23—C24B | 105.7 (11) |
N1—Sn1—C10—C11B | −78.5 (8) | O1—Sn2—C23—C24B | −177.3 (11) |
C10—Sn1—C12—C13 | −79.3 (5) | Cl1—Sn2—C23—C24B | 11.9 (11) |
O2—Sn1—C12—C13 | 17.2 (4) | O3—Sn2—C23—C24A | −131.5 (10) |
O1—Sn1—C12—C13 | 177.3 (4) | O4—Sn2—C23—C24A | 59.1 (10) |
N1—Sn1—C12—C13 | 98.9 (4) | O1—Sn2—C23—C24A | 136.1 (10) |
C1—O1—Sn2—O3 | −13.4 (3) | Cl1—Sn2—C23—C24A | −34.7 (10) |
Sn1—O1—Sn2—O3 | 172.42 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cl1i | 0.93 | 2.86 | 3.637 (5) | 142 |
C2—H2B···O3ii | 0.97 | 2.67 | 3.510 (6) | 146 |
C3—H3···O3ii | 0.93 | 2.54 | 3.328 (5) | 143 |
Symmetry codes: (i) x, y, z−1; (ii) x, −y+1/2, z−1/2. |
(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 = 680.31 | Dx = 1.772 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9924 reflections |
a = 13.2848 (3) Å | θ = 2.5–34.8° |
b = 15.7966 (4) Å | µ = 2.10 mm−1 |
c = 25.7287 (6) Å | T = 93 K |
β = 109.176 (1)° | Prism, pale yellow |
V = 5099.7 (2) Å3 | 0.26 × 0.24 × 0.13 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 12288 independent reflections |
Radiation source: fine-focus sealed tube | 9971 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 28.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.612, Tmax = 0.772 | k = −20→20 |
46297 measured reflections | l = −33→33 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-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 parameters | Δρmax = 1.21 e Å−3 |
0 restraints | Δρmin = −0.88 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Sn1 | 0.549813 (17) | 0.534661 (14) | 0.648549 (9) | 0.01411 (5) | |
Sn2 | 0.312288 (17) | 0.389744 (14) | 0.642427 (9) | 0.01301 (5) | |
Cl1 | 0.12061 (6) | 0.38946 (5) | 0.63071 (3) | 0.01894 (17) | |
O1 | 0.47299 (17) | 0.41165 (14) | 0.64314 (9) | 0.0176 (5) | |
O2 | 0.67731 (18) | 0.62136 (14) | 0.65933 (10) | 0.0209 (5) | |
O3 | 0.31995 (18) | 0.26281 (14) | 0.63131 (9) | 0.0182 (5) | |
O4 | 0.31214 (17) | 0.51690 (13) | 0.62207 (9) | 0.0152 (5) | |
N1 | 0.6799 (2) | 0.44533 (17) | 0.67493 (11) | 0.0159 (6) | |
N2 | 0.2620 (2) | 0.37979 (17) | 0.55130 (11) | 0.0157 (6) | |
C1 | 0.5432 (3) | 0.3401 (2) | 0.65044 (14) | 0.0190 (7) | |
H1A | 0.5522 | 0.3247 | 0.6149 | 0.023* | |
H1B | 0.5128 | 0.2908 | 0.6639 | 0.023* | |
C2 | 0.6490 (3) | 0.3635 (2) | 0.69160 (14) | 0.0187 (7) | |
H2A | 0.6431 | 0.3676 | 0.7289 | 0.022* | |
H2B | 0.7030 | 0.3200 | 0.6922 | 0.022* | |
C3 | 0.7714 (3) | 0.4520 (2) | 0.66762 (13) | 0.0169 (7) | |
H3 | 0.8129 | 0.4019 | 0.6721 | 0.020* | |
C4 | 0.8165 (3) | 0.5277 (2) | 0.65345 (13) | 0.0162 (7) | |
C5 | 0.7704 (3) | 0.6088 (2) | 0.65215 (13) | 0.0173 (7) | |
C6 | 0.8292 (3) | 0.6790 (2) | 0.64388 (15) | 0.0237 (8) | |
H6 | 0.8021 | 0.7345 | 0.6444 | 0.028* | |
C7 | 0.9254 (3) | 0.6684 (2) | 0.63509 (14) | 0.0234 (8) | |
H7 | 0.9626 | 0.7167 | 0.6290 | 0.028* | |
C8 | 0.9691 (3) | 0.5881 (2) | 0.63499 (14) | 0.0225 (8) | |
H8 | 1.0348 | 0.5814 | 0.6282 | 0.027* | |
C9 | 0.9157 (3) | 0.5196 (2) | 0.64482 (14) | 0.0189 (7) | |
H9 | 0.9460 | 0.4648 | 0.6459 | 0.023* | |
C10 | 0.4896 (3) | 0.5546 (2) | 0.56298 (14) | 0.0195 (7) | |
H10 | 0.4241 | 0.5283 | 0.5427 | 0.023* | |
C11 | 0.5381 (3) | 0.6020 (2) | 0.53577 (15) | 0.0253 (8) | |
H11A | 0.6036 | 0.6291 | 0.5550 | 0.030* | |
H11B | 0.5072 | 0.6088 | 0.4971 | 0.030* | |
C12 | 0.5065 (3) | 0.5916 (2) | 0.71216 (13) | 0.0184 (7) | |
H12 | 0.4595 | 0.5622 | 0.7269 | 0.022* | |
C13 | 0.5422 (3) | 0.6666 (2) | 0.73220 (15) | 0.0273 (8) | |
H13A | 0.5892 | 0.6969 | 0.7180 | 0.033* | |
H13B | 0.5210 | 0.6904 | 0.7609 | 0.033* | |
C14 | 0.2649 (3) | 0.2343 (2) | 0.57758 (14) | 0.0222 (8) | |
H14A | 0.1879 | 0.2298 | 0.5725 | 0.027* | |
H14B | 0.2909 | 0.1772 | 0.5724 | 0.027* | |
C15 | 0.2808 (3) | 0.2946 (2) | 0.53447 (14) | 0.0217 (7) | |
H15A | 0.3541 | 0.2896 | 0.5331 | 0.026* | |
H15B | 0.2298 | 0.2813 | 0.4976 | 0.026* | |
C16 | 0.2026 (3) | 0.4327 (2) | 0.51718 (13) | 0.0179 (7) | |
H16 | 0.1720 | 0.4153 | 0.4799 | 0.021* | |
C17 | 0.1791 (3) | 0.5171 (2) | 0.53151 (13) | 0.0144 (7) | |
C18 | 0.2353 (3) | 0.5558 (2) | 0.58261 (13) | 0.0147 (7) | |
C19 | 0.2115 (3) | 0.6395 (2) | 0.59099 (14) | 0.0181 (7) | |
H19 | 0.2521 | 0.6678 | 0.6238 | 0.022* | |
C20 | 0.1301 (3) | 0.6819 (2) | 0.55245 (14) | 0.0200 (7) | |
H20 | 0.1140 | 0.7385 | 0.5596 | 0.024* | |
C21 | 0.0710 (3) | 0.6433 (2) | 0.50321 (15) | 0.0216 (7) | |
H21 | 0.0134 | 0.6723 | 0.4773 | 0.026* | |
C22 | 0.0974 (3) | 0.5629 (2) | 0.49285 (14) | 0.0188 (7) | |
H22 | 0.0596 | 0.5373 | 0.4586 | 0.023* | |
C23 | 0.3655 (3) | 0.4022 (2) | 0.72923 (14) | 0.0219 (8) | |
H23 | 0.4321 | 0.3782 | 0.7501 | 0.026* | |
C24 | 0.3089 (3) | 0.4424 (3) | 0.75503 (15) | 0.0323 (9) | |
H24A | 0.2422 | 0.4667 | 0.7347 | 0.039* | |
H24B | 0.3348 | 0.4470 | 0.7940 | 0.039* | |
Sn3 | −0.018842 (17) | 1.000517 (14) | 0.345004 (9) | 0.01500 (5) | |
Sn4 | 0.221667 (17) | 0.860189 (14) | 0.359981 (9) | 0.01325 (5) | |
Cl2 | 0.41239 (6) | 0.86687 (5) | 0.37278 (3) | 0.01977 (17) | |
O5 | 0.05779 (17) | 0.87819 (14) | 0.35584 (9) | 0.0165 (5) | |
O6 | −0.14574 (19) | 1.08758 (15) | 0.32863 (10) | 0.0224 (5) | |
O7 | 0.21999 (18) | 0.73729 (14) | 0.38281 (9) | 0.0186 (5) | |
O8 | 0.21394 (18) | 0.99057 (14) | 0.36727 (9) | 0.0174 (5) | |
N3 | −0.1487 (2) | 0.91014 (17) | 0.32389 (11) | 0.0175 (6) | |
N4 | 0.2651 (2) | 0.87111 (18) | 0.45077 (11) | 0.0168 (6) | |
C25 | −0.0099 (3) | 0.8069 (2) | 0.35397 (14) | 0.0187 (7) | |
H25A | −0.0172 | 0.7976 | 0.3906 | 0.022* | |
H25B | 0.0213 | 0.7553 | 0.3436 | 0.022* | |
C26 | −0.1177 (3) | 0.8247 (2) | 0.31191 (15) | 0.0204 (7) | |
H26A | −0.1135 | 0.8224 | 0.2742 | 0.025* | |
H26B | −0.1706 | 0.7824 | 0.3149 | 0.025* | |
C27 | −0.2405 (3) | 0.9209 (2) | 0.33044 (13) | 0.0179 (7) | |
H27 | −0.2839 | 0.8721 | 0.3271 | 0.021* | |
C28 | −0.2830 (3) | 0.9995 (2) | 0.34233 (14) | 0.0186 (7) | |
C29 | −0.2351 (3) | 1.0788 (2) | 0.33999 (13) | 0.0172 (7) | |
C30 | −0.2891 (3) | 1.1516 (2) | 0.34756 (15) | 0.0245 (8) | |
H30 | −0.2611 | 1.2058 | 0.3440 | 0.029* | |
C31 | −0.3822 (3) | 1.1459 (3) | 0.36011 (14) | 0.0267 (8) | |
H31 | −0.4155 | 1.1962 | 0.3666 | 0.032* | |
C32 | −0.4281 (3) | 1.0676 (2) | 0.36338 (14) | 0.0248 (8) | |
H32 | −0.4922 | 1.0642 | 0.3721 | 0.030* | |
C33 | −0.3796 (3) | 0.9962 (2) | 0.35384 (14) | 0.0221 (8) | |
H33 | −0.4116 | 0.9428 | 0.3550 | 0.026* | |
C34 | 0.0382 (3) | 1.0274 (2) | 0.42993 (14) | 0.0235 (8) | |
H34 | 0.0909 | 0.9910 | 0.4530 | 0.028* | |
C35 | 0.0059 (4) | 1.0907 (3) | 0.45281 (18) | 0.0461 (12) | |
H35A | −0.0467 | 1.1284 | 0.4309 | 0.055* | |
H35B | 0.0351 | 1.0992 | 0.4914 | 0.055* | |
C36 | 0.0268 (3) | 1.0489 (2) | 0.27989 (13) | 0.0190 (7) | |
H36 | 0.0647 | 1.0133 | 0.2630 | 0.023* | |
C37 | 0.0045 (3) | 1.1269 (2) | 0.26182 (15) | 0.0275 (8) | |
H37A | −0.0334 | 1.1633 | 0.2783 | 0.033* | |
H37B | 0.0263 | 1.1468 | 0.2323 | 0.033* | |
C38 | 0.2736 (3) | 0.7213 (2) | 0.43907 (14) | 0.0232 (8) | |
H38A | 0.3513 | 0.7186 | 0.4458 | 0.028* | |
H38B | 0.2506 | 0.6658 | 0.4492 | 0.028* | |
C39 | 0.2500 (3) | 0.7902 (2) | 0.47467 (14) | 0.0223 (8) | |
H39A | 0.1759 | 0.7851 | 0.4749 | 0.027* | |
H39B | 0.2991 | 0.7856 | 0.5130 | 0.027* | |
C40 | 0.3133 (3) | 0.9329 (2) | 0.48066 (14) | 0.0193 (7) | |
H40 | 0.3386 | 0.9248 | 0.5194 | 0.023* | |
C41 | 0.3321 (3) | 1.0144 (2) | 0.45987 (14) | 0.0176 (7) | |
C42 | 0.2834 (3) | 1.0388 (2) | 0.40405 (14) | 0.0171 (7) | |
C43 | 0.3082 (3) | 1.1182 (2) | 0.38777 (15) | 0.0218 (7) | |
H43 | 0.2755 | 1.1361 | 0.3508 | 0.026* | |
C44 | 0.3799 (3) | 1.1717 (2) | 0.42475 (16) | 0.0250 (8) | |
H44 | 0.3969 | 1.2249 | 0.4125 | 0.030* | |
C45 | 0.4273 (3) | 1.1480 (2) | 0.47958 (16) | 0.0258 (8) | |
H45 | 0.4759 | 1.1849 | 0.5048 | 0.031* | |
C46 | 0.4027 (3) | 1.0706 (2) | 0.49659 (14) | 0.0229 (8) | |
H46 | 0.4341 | 1.0546 | 0.5340 | 0.027* | |
C47 | 0.1661 (3) | 0.8460 (2) | 0.27306 (14) | 0.0213 (7) | |
H47 | 0.0914 | 0.8406 | 0.2554 | 0.026* | |
C48 | 0.2265 (3) | 0.8441 (3) | 0.24207 (16) | 0.0376 (11) | |
H48A | 0.3016 | 0.8493 | 0.2582 | 0.045* | |
H48B | 0.1953 | 0.8375 | 0.2034 | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.01062 (11) | 0.01293 (11) | 0.01778 (11) | 0.00204 (8) | 0.00330 (9) | −0.00089 (9) |
Sn2 | 0.01083 (11) | 0.01327 (11) | 0.01486 (11) | 0.00067 (8) | 0.00414 (8) | 0.00037 (8) |
Cl1 | 0.0122 (4) | 0.0214 (4) | 0.0236 (4) | 0.0016 (3) | 0.0064 (3) | 0.0024 (3) |
O1 | 0.0088 (11) | 0.0176 (13) | 0.0262 (13) | 0.0011 (9) | 0.0055 (10) | 0.0004 (10) |
O2 | 0.0111 (12) | 0.0148 (13) | 0.0369 (15) | 0.0006 (9) | 0.0080 (10) | −0.0044 (10) |
O3 | 0.0179 (12) | 0.0144 (12) | 0.0216 (12) | 0.0017 (9) | 0.0057 (10) | 0.0014 (9) |
O4 | 0.0141 (11) | 0.0113 (12) | 0.0178 (11) | 0.0003 (9) | 0.0019 (9) | −0.0003 (9) |
N1 | 0.0112 (13) | 0.0132 (14) | 0.0224 (15) | 0.0018 (10) | 0.0042 (11) | 0.0015 (11) |
N2 | 0.0182 (14) | 0.0134 (14) | 0.0165 (14) | −0.0019 (11) | 0.0071 (11) | −0.0023 (11) |
C1 | 0.0155 (17) | 0.0138 (17) | 0.0296 (19) | 0.0019 (13) | 0.0102 (15) | 0.0001 (14) |
C2 | 0.0136 (16) | 0.0159 (17) | 0.0258 (18) | 0.0046 (13) | 0.0054 (14) | 0.0075 (14) |
C3 | 0.0122 (16) | 0.0158 (17) | 0.0197 (17) | 0.0021 (13) | 0.0012 (13) | −0.0016 (13) |
C4 | 0.0093 (15) | 0.0203 (18) | 0.0167 (16) | 0.0020 (13) | 0.0010 (12) | −0.0014 (13) |
C5 | 0.0128 (16) | 0.0175 (17) | 0.0196 (17) | −0.0003 (13) | 0.0025 (13) | −0.0027 (13) |
C6 | 0.0204 (18) | 0.0173 (18) | 0.028 (2) | 0.0006 (14) | 0.0010 (15) | −0.0004 (15) |
C7 | 0.0176 (18) | 0.024 (2) | 0.0256 (19) | −0.0065 (15) | 0.0034 (15) | 0.0008 (15) |
C8 | 0.0145 (17) | 0.033 (2) | 0.0196 (17) | −0.0017 (15) | 0.0046 (14) | −0.0024 (15) |
C9 | 0.0149 (17) | 0.0204 (19) | 0.0210 (17) | 0.0036 (13) | 0.0054 (14) | −0.0001 (14) |
C10 | 0.0179 (17) | 0.0204 (19) | 0.0193 (17) | 0.0013 (13) | 0.0046 (14) | 0.0008 (14) |
C11 | 0.034 (2) | 0.0179 (19) | 0.0228 (18) | −0.0016 (16) | 0.0081 (16) | −0.0019 (15) |
C12 | 0.0149 (17) | 0.0212 (19) | 0.0174 (16) | 0.0019 (13) | 0.0032 (13) | −0.0027 (13) |
C13 | 0.027 (2) | 0.027 (2) | 0.026 (2) | 0.0004 (16) | 0.0064 (16) | −0.0053 (16) |
C14 | 0.028 (2) | 0.0147 (18) | 0.0255 (19) | −0.0004 (14) | 0.0105 (16) | −0.0024 (14) |
C15 | 0.028 (2) | 0.0141 (18) | 0.0254 (19) | −0.0011 (14) | 0.0123 (16) | −0.0021 (14) |
C16 | 0.0184 (17) | 0.0195 (18) | 0.0152 (16) | −0.0049 (14) | 0.0048 (13) | −0.0007 (13) |
C17 | 0.0146 (16) | 0.0117 (16) | 0.0188 (16) | −0.0005 (12) | 0.0079 (13) | 0.0025 (12) |
C18 | 0.0124 (15) | 0.0155 (17) | 0.0177 (16) | −0.0021 (12) | 0.0071 (13) | 0.0019 (12) |
C19 | 0.0210 (18) | 0.0157 (17) | 0.0190 (17) | −0.0006 (13) | 0.0085 (14) | 0.0006 (13) |
C20 | 0.0253 (19) | 0.0122 (17) | 0.0263 (19) | 0.0030 (14) | 0.0134 (15) | 0.0035 (14) |
C21 | 0.0142 (17) | 0.0230 (19) | 0.0260 (19) | 0.0032 (14) | 0.0044 (14) | 0.0091 (15) |
C22 | 0.0148 (17) | 0.0199 (19) | 0.0195 (17) | −0.0033 (13) | 0.0028 (14) | 0.0052 (14) |
C23 | 0.0236 (19) | 0.0216 (19) | 0.0164 (17) | 0.0002 (14) | 0.0012 (14) | 0.0028 (14) |
C24 | 0.030 (2) | 0.048 (3) | 0.0207 (19) | 0.0011 (19) | 0.0103 (17) | −0.0008 (17) |
Sn3 | 0.01362 (11) | 0.01276 (11) | 0.01892 (11) | −0.00165 (9) | 0.00573 (9) | 0.00031 (9) |
Sn4 | 0.01175 (11) | 0.01319 (11) | 0.01467 (11) | −0.00046 (8) | 0.00413 (8) | −0.00020 (8) |
Cl2 | 0.0135 (4) | 0.0195 (4) | 0.0272 (4) | −0.0010 (3) | 0.0080 (3) | −0.0016 (3) |
O5 | 0.0113 (11) | 0.0115 (12) | 0.0264 (13) | −0.0031 (9) | 0.0057 (10) | 0.0001 (9) |
O6 | 0.0185 (13) | 0.0153 (13) | 0.0352 (14) | 0.0017 (10) | 0.0112 (11) | 0.0045 (10) |
O7 | 0.0194 (12) | 0.0139 (12) | 0.0215 (12) | −0.0001 (9) | 0.0053 (10) | 0.0035 (10) |
O8 | 0.0137 (11) | 0.0173 (13) | 0.0190 (12) | −0.0005 (9) | 0.0023 (9) | −0.0015 (9) |
N3 | 0.0131 (14) | 0.0151 (15) | 0.0226 (15) | −0.0018 (11) | 0.0034 (12) | 0.0008 (11) |
N4 | 0.0147 (14) | 0.0188 (15) | 0.0163 (14) | 0.0013 (11) | 0.0043 (11) | 0.0014 (11) |
C25 | 0.0142 (16) | 0.0136 (17) | 0.0270 (19) | −0.0037 (13) | 0.0052 (14) | −0.0022 (14) |
C26 | 0.0165 (17) | 0.0140 (17) | 0.0291 (19) | −0.0012 (13) | 0.0052 (15) | −0.0012 (14) |
C27 | 0.0138 (16) | 0.0197 (18) | 0.0195 (17) | −0.0036 (13) | 0.0045 (13) | 0.0049 (14) |
C28 | 0.0133 (16) | 0.0226 (19) | 0.0185 (16) | 0.0022 (14) | 0.0032 (13) | 0.0014 (14) |
C29 | 0.0163 (17) | 0.0198 (18) | 0.0141 (16) | 0.0009 (13) | 0.0030 (13) | 0.0016 (13) |
C30 | 0.028 (2) | 0.0179 (19) | 0.0258 (19) | 0.0048 (15) | 0.0057 (16) | −0.0021 (15) |
C31 | 0.023 (2) | 0.033 (2) | 0.0212 (18) | 0.0136 (16) | 0.0046 (15) | −0.0044 (16) |
C32 | 0.0173 (18) | 0.039 (2) | 0.0167 (17) | 0.0057 (16) | 0.0032 (14) | −0.0033 (15) |
C33 | 0.0129 (17) | 0.032 (2) | 0.0196 (17) | 0.0003 (15) | 0.0032 (14) | 0.0012 (15) |
C34 | 0.0213 (19) | 0.028 (2) | 0.0219 (18) | 0.0022 (15) | 0.0086 (15) | −0.0004 (15) |
C35 | 0.065 (3) | 0.040 (3) | 0.027 (2) | 0.019 (2) | 0.006 (2) | −0.0042 (19) |
C36 | 0.0172 (17) | 0.0210 (18) | 0.0171 (16) | −0.0023 (13) | 0.0032 (14) | 0.0020 (14) |
C37 | 0.030 (2) | 0.025 (2) | 0.026 (2) | −0.0039 (16) | 0.0068 (16) | 0.0045 (16) |
C38 | 0.0213 (18) | 0.023 (2) | 0.0253 (19) | −0.0003 (15) | 0.0078 (15) | 0.0069 (15) |
C39 | 0.0248 (19) | 0.0229 (19) | 0.0192 (17) | −0.0007 (15) | 0.0073 (15) | 0.0066 (14) |
C40 | 0.0145 (17) | 0.0256 (19) | 0.0156 (16) | 0.0049 (14) | 0.0021 (13) | −0.0007 (14) |
C41 | 0.0127 (16) | 0.0155 (18) | 0.0235 (18) | 0.0024 (13) | 0.0047 (14) | −0.0040 (13) |
C42 | 0.0105 (15) | 0.0183 (17) | 0.0232 (17) | 0.0028 (13) | 0.0063 (13) | −0.0035 (14) |
C43 | 0.0192 (18) | 0.0168 (18) | 0.0280 (19) | 0.0019 (14) | 0.0060 (15) | −0.0012 (14) |
C44 | 0.0194 (18) | 0.0142 (18) | 0.043 (2) | −0.0005 (14) | 0.0121 (17) | −0.0054 (16) |
C45 | 0.0117 (17) | 0.024 (2) | 0.038 (2) | −0.0008 (14) | 0.0027 (15) | −0.0162 (17) |
C46 | 0.0141 (17) | 0.029 (2) | 0.0218 (18) | 0.0027 (15) | 0.0003 (14) | −0.0098 (15) |
C47 | 0.0245 (19) | 0.0201 (19) | 0.0166 (17) | 0.0026 (14) | 0.0032 (14) | −0.0015 (14) |
C48 | 0.037 (2) | 0.057 (3) | 0.0196 (19) | 0.018 (2) | 0.0096 (18) | 0.0030 (19) |
Geometric parameters (Å, º) top
Sn1—C10 | 2.105 (3) | Sn3—C36 | 2.104 (3) |
Sn1—C12 | 2.107 (3) | Sn3—C34 | 2.108 (4) |
Sn1—O2 | 2.124 (2) | Sn3—O6 | 2.108 (2) |
Sn1—N1 | 2.161 (3) | Sn3—O5 | 2.159 (2) |
Sn1—O1 | 2.178 (2) | Sn3—N3 | 2.167 (3) |
Sn2—O3 | 2.033 (2) | Sn4—O7 | 2.030 (2) |
Sn2—O4 | 2.076 (2) | Sn4—O8 | 2.074 (2) |
Sn2—C23 | 2.119 (3) | Sn4—C47 | 2.124 (3) |
Sn2—O1 | 2.157 (2) | Sn4—O5 | 2.163 (2) |
Sn2—N2 | 2.222 (3) | Sn4—N4 | 2.221 (3) |
Sn2—Cl1 | 2.4639 (10) | Sn4—Cl2 | 2.4477 (10) |
O1—C1 | 1.438 (4) | O5—C25 | 1.431 (4) |
O2—C5 | 1.324 (4) | O6—C29 | 1.320 (4) |
O3—C14 | 1.409 (4) | O7—C38 | 1.410 (4) |
O4—C18 | 1.330 (4) | O8—C42 | 1.324 (4) |
N1—C3 | 1.294 (4) | N3—C27 | 1.295 (4) |
N1—C2 | 1.462 (4) | N3—C26 | 1.472 (4) |
N2—C16 | 1.279 (4) | N4—C40 | 1.277 (4) |
N2—C15 | 1.460 (4) | N4—C39 | 1.460 (4) |
C1—C2 | 1.502 (5) | C25—C26 | 1.512 (5) |
C1—H1A | 0.9900 | C25—H25A | 0.9900 |
C1—H1B | 0.9900 | C25—H25B | 0.9900 |
C2—H2A | 0.9900 | C26—H26A | 0.9900 |
C2—H2B | 0.9900 | C26—H26B | 0.9900 |
C3—C4 | 1.436 (5) | C27—C28 | 1.438 (5) |
C3—H3 | 0.9500 | C27—H27 | 0.9500 |
C4—C9 | 1.413 (4) | C28—C33 | 1.410 (5) |
C4—C5 | 1.415 (5) | C28—C29 | 1.414 (5) |
C5—C6 | 1.413 (5) | C29—C30 | 1.403 (5) |
C6—C7 | 1.379 (5) | C30—C31 | 1.379 (5) |
C6—H6 | 0.9500 | C30—H30 | 0.9500 |
C7—C8 | 1.395 (5) | C31—C32 | 1.394 (6) |
C7—H7 | 0.9500 | C31—H31 | 0.9500 |
C8—C9 | 1.363 (5) | C32—C33 | 1.361 (5) |
C8—H8 | 0.9500 | C32—H32 | 0.9500 |
C9—H9 | 0.9500 | C33—H33 | 0.9500 |
C10—C11 | 1.327 (5) | C34—C35 | 1.302 (5) |
C10—H10 | 0.9500 | C34—H34 | 0.9500 |
C11—H11A | 0.9500 | C35—H35A | 0.9500 |
C11—H11B | 0.9500 | C35—H35B | 0.9500 |
C12—C13 | 1.317 (5) | C36—C37 | 1.315 (5) |
C12—H12 | 0.9500 | C36—H36 | 0.9500 |
C13—H13A | 0.9500 | C37—H37A | 0.9500 |
C13—H13B | 0.9500 | C37—H37B | 0.9500 |
C14—C15 | 1.528 (5) | C38—C39 | 1.521 (5) |
C14—H14A | 0.9900 | C38—H38A | 0.9900 |
C14—H14B | 0.9900 | C38—H38B | 0.9900 |
C15—H15A | 0.9900 | C39—H39A | 0.9900 |
C15—H15B | 0.9900 | C39—H39B | 0.9900 |
C16—C17 | 1.444 (5) | C40—C41 | 1.447 (5) |
C16—H16 | 0.9500 | C40—H40 | 0.9500 |
C17—C22 | 1.408 (4) | C41—C46 | 1.406 (5) |
C17—C18 | 1.420 (4) | C41—C42 | 1.421 (5) |
C18—C19 | 1.393 (5) | C42—C43 | 1.396 (5) |
C19—C20 | 1.377 (5) | C43—C44 | 1.390 (5) |
C19—H19 | 0.9500 | C43—H43 | 0.9500 |
C20—C21 | 1.393 (5) | C44—C45 | 1.394 (5) |
C20—H20 | 0.9500 | C44—H44 | 0.9500 |
C21—C22 | 1.367 (5) | C45—C46 | 1.375 (5) |
C21—H21 | 0.9500 | C45—H45 | 0.9500 |
C22—H22 | 0.9500 | C46—H46 | 0.9500 |
C23—C24 | 1.318 (5) | C47—C48 | 1.304 (5) |
C23—H23 | 0.9500 | C47—H47 | 0.9500 |
C24—H24A | 0.9500 | C48—H48A | 0.9500 |
C24—H24B | 0.9500 | C48—H48B | 0.9500 |
| | | |
C10—Sn1—C12 | 129.90 (13) | C36—Sn3—C34 | 130.76 (14) |
C10—Sn1—O2 | 93.02 (12) | C36—Sn3—O6 | 91.41 (12) |
C12—Sn1—O2 | 91.88 (12) | C34—Sn3—O6 | 93.85 (12) |
C10—Sn1—N1 | 114.62 (12) | C36—Sn3—O5 | 100.43 (11) |
C12—Sn1—N1 | 115.43 (12) | C34—Sn3—O5 | 93.03 (12) |
O2—Sn1—N1 | 81.89 (10) | O6—Sn3—O5 | 157.20 (9) |
C10—Sn1—O1 | 93.31 (11) | C36—Sn3—N3 | 116.99 (12) |
C12—Sn1—O1 | 100.88 (11) | C34—Sn3—N3 | 112.23 (13) |
O2—Sn1—O1 | 156.97 (8) | O6—Sn3—N3 | 82.01 (10) |
N1—Sn1—O1 | 75.34 (9) | O5—Sn3—N3 | 75.26 (9) |
O3—Sn2—O4 | 156.21 (9) | O7—Sn4—O8 | 156.62 (9) |
O3—Sn2—C23 | 103.03 (11) | O7—Sn4—C47 | 99.81 (11) |
O4—Sn2—C23 | 98.52 (11) | O8—Sn4—C47 | 100.95 (11) |
O3—Sn2—O1 | 93.69 (9) | O7—Sn4—O5 | 91.92 (9) |
O4—Sn2—O1 | 76.46 (9) | O8—Sn4—O5 | 78.17 (8) |
C23—Sn2—O1 | 89.38 (12) | C47—Sn4—O5 | 88.05 (12) |
O3—Sn2—N2 | 78.07 (9) | O7—Sn4—N4 | 78.10 (10) |
O4—Sn2—N2 | 80.05 (9) | O8—Sn4—N4 | 80.29 (10) |
C23—Sn2—N2 | 177.70 (12) | C47—Sn4—N4 | 174.74 (12) |
O1—Sn2—N2 | 88.53 (10) | O5—Sn4—N4 | 87.20 (10) |
O3—Sn2—Cl1 | 94.50 (7) | O7—Sn4—Cl2 | 96.40 (7) |
O4—Sn2—Cl1 | 93.19 (7) | O8—Sn4—Cl2 | 91.42 (7) |
C23—Sn2—Cl1 | 95.91 (11) | C47—Sn4—Cl2 | 97.62 (11) |
O1—Sn2—Cl1 | 169.00 (6) | O5—Sn4—Cl2 | 168.97 (6) |
N2—Sn2—Cl1 | 85.99 (8) | N4—Sn4—Cl2 | 87.44 (8) |
C1—O1—Sn2 | 118.19 (19) | C25—O5—Sn3 | 115.81 (18) |
C1—O1—Sn1 | 115.03 (18) | C25—O5—Sn4 | 120.59 (19) |
Sn2—O1—Sn1 | 125.83 (10) | Sn3—O5—Sn4 | 123.24 (10) |
C5—O2—Sn1 | 128.8 (2) | C29—O6—Sn3 | 127.3 (2) |
C14—O3—Sn2 | 114.83 (19) | C38—O7—Sn4 | 114.8 (2) |
C18—O4—Sn2 | 125.2 (2) | C42—O8—Sn4 | 126.3 (2) |
C3—N1—C2 | 118.8 (3) | C27—N3—C26 | 119.2 (3) |
C3—N1—Sn1 | 126.4 (2) | C27—N3—Sn3 | 125.9 (2) |
C2—N1—Sn1 | 113.4 (2) | C26—N3—Sn3 | 113.7 (2) |
C16—N2—C15 | 121.7 (3) | C40—N4—C39 | 121.8 (3) |
C16—N2—Sn2 | 125.6 (2) | C40—N4—Sn4 | 126.7 (2) |
C15—N2—Sn2 | 110.9 (2) | C39—N4—Sn4 | 110.5 (2) |
O1—C1—C2 | 108.3 (3) | O5—C25—C26 | 108.4 (3) |
O1—C1—H1A | 110.0 | O5—C25—H25A | 110.0 |
C2—C1—H1A | 110.0 | C26—C25—H25A | 110.0 |
O1—C1—H1B | 110.0 | O5—C25—H25B | 110.0 |
C2—C1—H1B | 110.0 | C26—C25—H25B | 110.0 |
H1A—C1—H1B | 108.4 | H25A—C25—H25B | 108.4 |
N1—C2—C1 | 107.4 (3) | N3—C26—C25 | 106.6 (3) |
N1—C2—H2A | 110.2 | N3—C26—H26A | 110.4 |
C1—C2—H2A | 110.2 | C25—C26—H26A | 110.4 |
N1—C2—H2B | 110.2 | N3—C26—H26B | 110.4 |
C1—C2—H2B | 110.2 | C25—C26—H26B | 110.4 |
H2A—C2—H2B | 108.5 | H26A—C26—H26B | 108.6 |
N1—C3—C4 | 126.5 (3) | N3—C27—C28 | 126.4 (3) |
N1—C3—H3 | 116.8 | N3—C27—H27 | 116.8 |
C4—C3—H3 | 116.8 | C28—C27—H27 | 116.8 |
C9—C4—C5 | 119.8 (3) | C33—C28—C29 | 119.7 (3) |
C9—C4—C3 | 116.9 (3) | C33—C28—C27 | 117.5 (3) |
C5—C4—C3 | 123.1 (3) | C29—C28—C27 | 122.8 (3) |
O2—C5—C6 | 119.4 (3) | O6—C29—C30 | 118.8 (3) |
O2—C5—C4 | 123.3 (3) | O6—C29—C28 | 123.5 (3) |
C6—C5—C4 | 117.2 (3) | C30—C29—C28 | 117.6 (3) |
C7—C6—C5 | 121.2 (3) | C31—C30—C29 | 121.1 (4) |
C7—C6—H6 | 119.4 | C31—C30—H30 | 119.4 |
C5—C6—H6 | 119.4 | C29—C30—H30 | 119.4 |
C6—C7—C8 | 121.3 (3) | C30—C31—C32 | 121.1 (3) |
C6—C7—H7 | 119.4 | C30—C31—H31 | 119.5 |
C8—C7—H7 | 119.4 | C32—C31—H31 | 119.5 |
C9—C8—C7 | 118.6 (3) | C33—C32—C31 | 118.8 (3) |
C9—C8—H8 | 120.7 | C33—C32—H32 | 120.6 |
C7—C8—H8 | 120.7 | C31—C32—H32 | 120.6 |
C8—C9—C4 | 121.8 (3) | C32—C33—C28 | 121.7 (4) |
C8—C9—H9 | 119.1 | C32—C33—H33 | 119.2 |
C4—C9—H9 | 119.1 | C28—C33—H33 | 119.2 |
C11—C10—Sn1 | 123.6 (3) | C35—C34—Sn3 | 124.3 (3) |
C11—C10—H10 | 118.2 | C35—C34—H34 | 117.8 |
Sn1—C10—H10 | 118.2 | Sn3—C34—H34 | 117.8 |
C10—C11—H11A | 120.0 | C34—C35—H35A | 120.0 |
C10—C11—H11B | 120.0 | C34—C35—H35B | 120.0 |
H11A—C11—H11B | 120.0 | H35A—C35—H35B | 120.0 |
C13—C12—Sn1 | 122.2 (3) | C37—C36—Sn3 | 122.1 (3) |
C13—C12—H12 | 118.9 | C37—C36—H36 | 119.0 |
Sn1—C12—H12 | 118.9 | Sn3—C36—H36 | 119.0 |
C12—C13—H13A | 120.0 | C36—C37—H37A | 120.0 |
C12—C13—H13B | 120.0 | C36—C37—H37B | 120.0 |
H13A—C13—H13B | 120.0 | H37A—C37—H37B | 120.0 |
O3—C14—C15 | 111.2 (3) | O7—C38—C39 | 110.8 (3) |
O3—C14—H14A | 109.4 | O7—C38—H38A | 109.5 |
C15—C14—H14A | 109.4 | C39—C38—H38A | 109.5 |
O3—C14—H14B | 109.4 | O7—C38—H38B | 109.5 |
C15—C14—H14B | 109.4 | C39—C38—H38B | 109.5 |
H14A—C14—H14B | 108.0 | H38A—C38—H38B | 108.1 |
N2—C15—C14 | 106.4 (3) | N4—C39—C38 | 106.8 (3) |
N2—C15—H15A | 110.5 | N4—C39—H39A | 110.4 |
C14—C15—H15A | 110.5 | C38—C39—H39A | 110.4 |
N2—C15—H15B | 110.5 | N4—C39—H39B | 110.4 |
C14—C15—H15B | 110.5 | C38—C39—H39B | 110.4 |
H15A—C15—H15B | 108.6 | H39A—C39—H39B | 108.6 |
N2—C16—C17 | 124.4 (3) | N4—C40—C41 | 124.8 (3) |
N2—C16—H16 | 117.8 | N4—C40—H40 | 117.6 |
C17—C16—H16 | 117.8 | C41—C40—H40 | 117.6 |
C22—C17—C18 | 118.8 (3) | C46—C41—C42 | 119.3 (3) |
C22—C17—C16 | 118.4 (3) | C46—C41—C40 | 118.1 (3) |
C18—C17—C16 | 122.8 (3) | C42—C41—C40 | 122.6 (3) |
O4—C18—C19 | 118.5 (3) | O8—C42—C43 | 118.7 (3) |
O4—C18—C17 | 123.1 (3) | O8—C42—C41 | 123.1 (3) |
C19—C18—C17 | 118.4 (3) | C43—C42—C41 | 118.2 (3) |
C20—C19—C18 | 121.0 (3) | C44—C43—C42 | 121.1 (3) |
C20—C19—H19 | 119.5 | C44—C43—H43 | 119.4 |
C18—C19—H19 | 119.5 | C42—C43—H43 | 119.4 |
C19—C20—C21 | 121.1 (3) | C43—C44—C45 | 120.7 (3) |
C19—C20—H20 | 119.4 | C43—C44—H44 | 119.7 |
C21—C20—H20 | 119.4 | C45—C44—H44 | 119.7 |
C22—C21—C20 | 118.7 (3) | C46—C45—C44 | 119.0 (3) |
C22—C21—H21 | 120.7 | C46—C45—H45 | 120.5 |
C20—C21—H21 | 120.7 | C44—C45—H45 | 120.5 |
C21—C22—C17 | 121.9 (3) | C45—C46—C41 | 121.6 (3) |
C21—C22—H22 | 119.1 | C45—C46—H46 | 119.2 |
C17—C22—H22 | 119.1 | C41—C46—H46 | 119.2 |
C24—C23—Sn2 | 121.9 (3) | C48—C47—Sn4 | 125.1 (3) |
C24—C23—H23 | 119.1 | C48—C47—H47 | 117.4 |
Sn2—C23—H23 | 119.1 | Sn4—C47—H47 | 117.4 |
C23—C24—H24A | 120.0 | C47—C48—H48A | 120.0 |
C23—C24—H24B | 120.0 | C47—C48—H48B | 120.0 |
H24A—C24—H24B | 120.0 | H48A—C48—H48B | 120.0 |
| | | |
O3—Sn2—O1—C1 | −15.4 (2) | C36—Sn3—O5—C25 | −126.1 (2) |
O4—Sn2—O1—C1 | −173.5 (2) | C34—Sn3—O5—C25 | 101.5 (2) |
C23—Sn2—O1—C1 | 87.6 (2) | O6—Sn3—O5—C25 | −6.0 (4) |
N2—Sn2—O1—C1 | −93.4 (2) | N3—Sn3—O5—C25 | −10.7 (2) |
Cl1—Sn2—O1—C1 | −153.4 (3) | C36—Sn3—O5—Sn4 | 47.00 (15) |
O3—Sn2—O1—Sn1 | 176.31 (13) | C34—Sn3—O5—Sn4 | −85.41 (15) |
O4—Sn2—O1—Sn1 | 18.24 (12) | O6—Sn3—O5—Sn4 | 167.16 (18) |
C23—Sn2—O1—Sn1 | −80.67 (15) | N3—Sn3—O5—Sn4 | 162.39 (15) |
N2—Sn2—O1—Sn1 | 98.36 (14) | O7—Sn4—O5—C25 | −16.3 (2) |
Cl1—Sn2—O1—Sn1 | 38.3 (4) | O8—Sn4—O5—C25 | −175.0 (2) |
C10—Sn1—O1—C1 | 105.2 (2) | C47—Sn4—O5—C25 | 83.4 (2) |
C12—Sn1—O1—C1 | −123.1 (2) | N4—Sn4—O5—C25 | −94.3 (2) |
O2—Sn1—O1—C1 | −0.5 (4) | Cl2—Sn4—O5—C25 | −155.3 (3) |
N1—Sn1—O1—C1 | −9.4 (2) | O7—Sn4—O5—Sn3 | 170.85 (13) |
C10—Sn1—O1—Sn2 | −86.18 (15) | O8—Sn4—O5—Sn3 | 12.20 (12) |
C12—Sn1—O1—Sn2 | 45.53 (16) | C47—Sn4—O5—Sn3 | −89.40 (15) |
O2—Sn1—O1—Sn2 | 168.07 (18) | N4—Sn4—O5—Sn3 | 92.86 (13) |
N1—Sn1—O1—Sn2 | 159.22 (15) | Cl2—Sn4—O5—Sn3 | 31.9 (4) |
C10—Sn1—O2—C5 | −82.3 (3) | C36—Sn3—O6—C29 | 154.0 (3) |
C12—Sn1—O2—C5 | 147.6 (3) | C34—Sn3—O6—C29 | −75.0 (3) |
N1—Sn1—O2—C5 | 32.2 (3) | O5—Sn3—O6—C29 | 32.3 (4) |
O1—Sn1—O2—C5 | 23.5 (4) | N3—Sn3—O6—C29 | 36.9 (3) |
O4—Sn2—O3—C14 | −40.3 (3) | O8—Sn4—O7—C38 | −40.1 (4) |
C23—Sn2—O3—C14 | 165.3 (2) | C47—Sn4—O7—C38 | 167.6 (2) |
O1—Sn2—O3—C14 | −104.4 (2) | O5—Sn4—O7—C38 | −104.1 (2) |
N2—Sn2—O3—C14 | −16.7 (2) | N4—Sn4—O7—C38 | −17.3 (2) |
Cl1—Sn2—O3—C14 | 68.2 (2) | Cl2—Sn4—O7—C38 | 68.7 (2) |
O3—Sn2—O4—C18 | 69.0 (3) | O7—Sn4—O8—C42 | 66.2 (4) |
C23—Sn2—O4—C18 | −136.2 (2) | C47—Sn4—O8—C42 | −141.6 (3) |
O1—Sn2—O4—C18 | 136.5 (2) | O5—Sn4—O8—C42 | 132.7 (3) |
N2—Sn2—O4—C18 | 45.7 (2) | N4—Sn4—O8—C42 | 43.6 (3) |
Cl1—Sn2—O4—C18 | −39.7 (2) | Cl2—Sn4—O8—C42 | −43.6 (2) |
C10—Sn1—N1—C3 | 60.6 (3) | C36—Sn3—N3—C27 | −116.3 (3) |
C12—Sn1—N1—C3 | −117.2 (3) | C34—Sn3—N3—C27 | 62.2 (3) |
O2—Sn1—N1—C3 | −29.0 (3) | O6—Sn3—N3—C27 | −28.8 (3) |
O1—Sn1—N1—C3 | 147.5 (3) | O5—Sn3—N3—C27 | 149.4 (3) |
C10—Sn1—N1—C2 | −105.8 (2) | C36—Sn3—N3—C26 | 76.6 (2) |
C12—Sn1—N1—C2 | 76.4 (2) | C34—Sn3—N3—C26 | −105.0 (2) |
O2—Sn1—N1—C2 | 164.6 (2) | O6—Sn3—N3—C26 | 164.1 (2) |
O1—Sn1—N1—C2 | −18.9 (2) | O5—Sn3—N3—C26 | −17.8 (2) |
O3—Sn2—N2—C16 | 154.2 (3) | O7—Sn4—N4—C40 | 158.8 (3) |
O4—Sn2—N2—C16 | −35.2 (3) | O8—Sn4—N4—C40 | −30.1 (3) |
C23—Sn2—N2—C16 | −87 (3) | C47—Sn4—N4—C40 | −134.2 (12) |
O1—Sn2—N2—C16 | −111.7 (3) | O5—Sn4—N4—C40 | −108.6 (3) |
Cl1—Sn2—N2—C16 | 58.7 (3) | Cl2—Sn4—N4—C40 | 61.7 (3) |
O3—Sn2—N2—C15 | −10.6 (2) | O7—Sn4—N4—C39 | −10.1 (2) |
O4—Sn2—N2—C15 | 160.0 (2) | O8—Sn4—N4—C39 | 161.0 (2) |
C23—Sn2—N2—C15 | 108 (3) | C47—Sn4—N4—C39 | 57.0 (13) |
O1—Sn2—N2—C15 | 83.5 (2) | O5—Sn4—N4—C39 | 82.5 (2) |
Cl1—Sn2—N2—C15 | −106.0 (2) | Cl2—Sn4—N4—C39 | −107.2 (2) |
Sn2—O1—C1—C2 | −135.0 (2) | Sn3—O5—C25—C26 | 35.9 (3) |
Sn1—O1—C1—C2 | 34.5 (3) | Sn4—O5—C25—C26 | −137.4 (2) |
C3—N1—C2—C1 | −125.0 (3) | C27—N3—C26—C25 | −127.0 (3) |
Sn1—N1—C2—C1 | 42.5 (3) | Sn3—N3—C26—C25 | 41.1 (3) |
O1—C1—C2—N1 | −49.0 (3) | O5—C25—C26—N3 | −48.6 (3) |
C2—N1—C3—C4 | −177.4 (3) | C26—N3—C27—C28 | 179.9 (3) |
Sn1—N1—C3—C4 | 16.9 (5) | Sn3—N3—C27—C28 | 13.4 (5) |
N1—C3—C4—C9 | −177.0 (3) | N3—C27—C28—C33 | −173.3 (3) |
N1—C3—C4—C5 | 8.1 (5) | N3—C27—C28—C29 | 10.1 (5) |
Sn1—O2—C5—C6 | 159.4 (2) | Sn3—O6—C29—C30 | 154.1 (2) |
Sn1—O2—C5—C4 | −22.0 (5) | Sn3—O6—C29—C28 | −29.2 (4) |
C9—C4—C5—O2 | 179.3 (3) | C33—C28—C29—O6 | −178.9 (3) |
C3—C4—C5—O2 | −5.8 (5) | C27—C28—C29—O6 | −2.4 (5) |
C9—C4—C5—C6 | −2.1 (5) | C33—C28—C29—C30 | −2.1 (5) |
C3—C4—C5—C6 | 172.8 (3) | C27—C28—C29—C30 | 174.4 (3) |
O2—C5—C6—C7 | −178.6 (3) | O6—C29—C30—C31 | −179.3 (3) |
C4—C5—C6—C7 | 2.7 (5) | C28—C29—C30—C31 | 3.8 (5) |
C5—C6—C7—C8 | −1.1 (5) | C29—C30—C31—C32 | −2.8 (5) |
C6—C7—C8—C9 | −1.2 (5) | C30—C31—C32—C33 | −0.1 (5) |
C7—C8—C9—C4 | 1.9 (5) | C31—C32—C33—C28 | 1.8 (5) |
C5—C4—C9—C8 | −0.2 (5) | C29—C28—C33—C32 | −0.6 (5) |
C3—C4—C9—C8 | −175.3 (3) | C27—C28—C33—C32 | −177.3 (3) |
C12—Sn1—C10—C11 | 100.7 (3) | C36—Sn3—C34—C35 | 84.2 (4) |
O2—Sn1—C10—C11 | 5.7 (3) | O6—Sn3—C34—C35 | −11.0 (4) |
N1—Sn1—C10—C11 | −76.8 (3) | O5—Sn3—C34—C35 | −169.3 (4) |
O1—Sn1—C10—C11 | −152.2 (3) | N3—Sn3—C34—C35 | −94.0 (4) |
C10—Sn1—C12—C13 | −80.9 (3) | C34—Sn3—C36—C37 | −71.2 (3) |
O2—Sn1—C12—C13 | 14.6 (3) | O6—Sn3—C36—C37 | 25.1 (3) |
N1—Sn1—C12—C13 | 96.6 (3) | O5—Sn3—C36—C37 | −174.5 (3) |
O1—Sn1—C12—C13 | 175.4 (3) | N3—Sn3—C36—C37 | 106.9 (3) |
Sn2—O3—C14—C15 | 40.9 (3) | Sn4—O7—C38—C39 | 41.5 (3) |
C16—N2—C15—C14 | −133.0 (3) | C40—N4—C39—C38 | −137.1 (3) |
Sn2—N2—C15—C14 | 32.4 (3) | Sn4—N4—C39—C38 | 32.4 (3) |
O3—C14—C15—N2 | −47.6 (4) | O7—C38—C39—N4 | −48.0 (4) |
C15—N2—C16—C17 | 178.6 (3) | C39—N4—C40—C41 | 179.3 (3) |
Sn2—N2—C16—C17 | 15.4 (5) | Sn4—N4—C40—C41 | 11.5 (5) |
N2—C16—C17—C22 | −168.2 (3) | N4—C40—C41—C46 | −168.6 (3) |
N2—C16—C17—C18 | 12.3 (5) | N4—C40—C41—C42 | 10.6 (5) |
Sn2—O4—C18—C19 | 144.7 (2) | Sn4—O8—C42—C43 | 142.1 (3) |
Sn2—O4—C18—C17 | −37.7 (4) | Sn4—O8—C42—C41 | −39.5 (4) |
C22—C17—C18—O4 | 178.6 (3) | C46—C41—C42—O8 | −178.1 (3) |
C16—C17—C18—O4 | −1.9 (5) | C40—C41—C42—O8 | 2.7 (5) |
C22—C17—C18—C19 | −3.8 (5) | C46—C41—C42—C43 | 0.3 (5) |
C16—C17—C18—C19 | 175.7 (3) | C40—C41—C42—C43 | −178.9 (3) |
O4—C18—C19—C20 | −177.5 (3) | O8—C42—C43—C44 | 179.5 (3) |
C17—C18—C19—C20 | 4.8 (5) | C41—C42—C43—C44 | 1.1 (5) |
C18—C19—C20—C21 | −1.9 (5) | C42—C43—C44—C45 | −1.5 (5) |
C19—C20—C21—C22 | −2.1 (5) | C43—C44—C45—C46 | 0.5 (5) |
C20—C21—C22—C17 | 3.0 (5) | C44—C45—C46—C41 | 0.9 (5) |
C18—C17—C22—C21 | 0.0 (5) | C42—C41—C46—C45 | −1.3 (5) |
C16—C17—C22—C21 | −179.5 (3) | C40—C41—C46—C45 | 177.9 (3) |
O3—Sn2—C23—C24 | −126.3 (3) | O7—Sn4—C47—C48 | −98.9 (4) |
O4—Sn2—C23—C24 | 63.8 (3) | O8—Sn4—C47—C48 | 92.0 (4) |
O1—Sn2—C23—C24 | 140.1 (3) | O5—Sn4—C47—C48 | 169.5 (4) |
N2—Sn2—C23—C24 | 115 (3) | N4—Sn4—C47—C48 | −165.0 (11) |
Cl1—Sn2—C23—C24 | −30.3 (3) | Cl2—Sn4—C47—C48 | −1.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O7i | 0.95 | 2.57 | 3.277 (4) | 131 |
C2—H2B···O7i | 0.99 | 2.62 | 3.379 (4) | 133 |
C27—H27···O3ii | 0.95 | 2.50 | 3.345 (4) | 148 |
C26—H26B···O3ii | 0.99 | 2.86 | 3.720 (4) | 146 |
C33—H33···Cl2iii | 0.95 | 2.80 | 3.596 (4) | 143 |
C9—H9···Cl1iv | 0.95 | 2.75 | 3.523 (3) | 139 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z. |