Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032958/hb2120sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032958/hb2120Isup2.hkl |
CCDC reference: 621333
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.028
- wR factor = 0.089
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.15 PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.20 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.26 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C15 - C16 ... 1.53 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
[Sn(C2H5)(C6H5)2(C6H4NO2)] | Z = 2 |
Mr = 424.05 | F(000) = 424 |
Triclinic, P1 | Dx = 1.543 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7562 (1) Å | Cell parameters from 6986 reflections |
b = 9.9711 (1) Å | θ = 2.6–33.3° |
c = 10.2908 (1) Å | µ = 1.41 mm−1 |
α = 78.990 (1)° | T = 173 K |
β = 77.066 (1)° | Plate, colourless |
γ = 70.622 (1)° | 0.38 × 0.20 × 0.10 mm |
V = 912.97 (2) Å3 |
Bruker APEXII CCD area-detector diffractometer | 4146 independent reflections |
Radiation source: fine-focus sealed tube | 3983 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.616, Tmax = 0.872 | k = −12→12 |
13345 measured reflections | l = −13→13 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.061P)2 + 0.7851P] where P = (Fo2 + 2Fc2)/3 |
4146 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 2.36 e Å−3 |
1 restraint | Δρmin = −1.10 e Å−3 |
Experimental. 1H NMR (CDCl3, δ, p.p.m.): –CH3 (1.48–1.51, triplet), –CH2 (1.80–1.88, quartet), –C6H5 (7.46–7.77, multiplet) and –C5H4N (7.90–8.75, multiplet); 19Sn NMR (CDCl3): -12.8 p.p.m. The crystal was measured to a 2θmax of 66° but only the reflections below 55° were used in the refinement. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.237601 (16) | 0.752294 (16) | 0.808295 (15) | 0.01265 (8) | |
O1 | 0.4750 (2) | 0.7242 (2) | 0.7935 (2) | 0.0160 (4) | |
O2 | 0.4087 (2) | 0.9411 (2) | 0.8670 (2) | 0.0201 (4) | |
N1 | 0.9689 (2) | 0.7820 (3) | 0.8049 (2) | 0.0159 (4) | |
C1 | 0.2946 (3) | 0.5438 (3) | 0.7448 (3) | 0.0145 (5) | |
C2 | 0.3259 (3) | 0.5202 (3) | 0.6081 (3) | 0.0171 (5) | |
C3 | 0.3673 (3) | 0.3814 (3) | 0.5710 (3) | 0.0213 (5) | |
C4 | 0.3770 (3) | 0.2627 (3) | 0.6717 (3) | 0.0213 (5) | |
C5 | 0.3454 (3) | 0.2832 (3) | 0.8084 (3) | 0.0199 (5) | |
C6 | 0.3037 (3) | 0.4222 (3) | 0.8443 (3) | 0.0167 (5) | |
C7 | 0.1881 (3) | 0.7271 (3) | 1.0279 (3) | 0.0156 (5) | |
C8 | 0.3059 (3) | 0.6940 (3) | 1.1003 (3) | 0.0183 (5) | |
C9 | 0.2823 (3) | 0.6684 (3) | 1.2419 (3) | 0.0217 (5) | |
C10 | 0.1398 (3) | 0.6743 (3) | 1.3147 (3) | 0.0204 (5) | |
C11 | 0.0230 (3) | 0.7040 (3) | 1.2454 (3) | 0.0206 (5) | |
C12 | 0.0463 (3) | 0.7307 (3) | 1.1035 (3) | 0.0192 (5) | |
C13 | 0.2042 (4) | 0.9442 (3) | 0.6636 (3) | 0.0255 (6) | |
C14 | 0.1409 (9) | 0.9505 (8) | 0.5389 (6) | 0.041 (2) | 0.54 (1) |
C14' | 0.3152 (7) | 0.9458 (7) | 0.5414 (6) | 0.022 (2) | 0.46 (1) |
C15 | 0.5034 (3) | 0.8322 (3) | 0.8259 (3) | 0.0140 (5) | |
C16 | 0.6680 (3) | 0.8152 (3) | 0.8127 (3) | 0.0132 (5) | |
C17 | 0.7114 (3) | 0.9273 (3) | 0.8393 (3) | 0.0156 (5) | |
C18 | 0.8621 (3) | 0.9067 (3) | 0.8330 (3) | 0.0175 (5) | |
C19 | 0.9263 (3) | 0.6752 (3) | 0.7780 (3) | 0.0178 (5) | |
C20 | 0.7778 (3) | 0.6872 (3) | 0.7806 (3) | 0.0159 (5) | |
H2 | 0.3187 | 0.5999 | 0.5398 | 0.021* | |
H3 | 0.3884 | 0.3680 | 0.4789 | 0.026* | |
H4 | 0.4049 | 0.1688 | 0.6475 | 0.026* | |
H5 | 0.3522 | 0.2031 | 0.8762 | 0.024* | |
H6 | 0.2812 | 0.4350 | 0.9366 | 0.020* | |
H8 | 0.4023 | 0.6892 | 1.0523 | 0.022* | |
H9 | 0.3624 | 0.6471 | 1.2883 | 0.026* | |
H10 | 0.1235 | 0.6581 | 1.4101 | 0.024* | |
H11 | −0.0727 | 0.7064 | 1.2940 | 0.025* | |
H12 | −0.0343 | 0.7513 | 1.0579 | 0.023* | |
H13a | 0.1385 | 1.0250 | 0.7123 | 0.031* | 0.54 (1) |
H13b | 0.3008 | 0.9625 | 0.6323 | 0.031* | 0.54 (1) |
H13c | 0.1080 | 0.9633 | 0.6358 | 0.031* | 0.46 (1) |
H13d | 0.1961 | 1.0252 | 0.7104 | 0.031* | 0.46 (1) |
H14a | 0.1323 | 1.0442 | 0.4847 | 0.062* | 0.54 (1) |
H14b | 0.0431 | 0.9366 | 0.5664 | 0.062* | 0.54 (1) |
H14c | 0.2065 | 0.8749 | 0.4856 | 0.062* | 0.54 (1) |
H14d | 0.2861 | 1.0384 | 0.4854 | 0.034* | 0.46 (1) |
H14e | 0.3227 | 0.8688 | 0.4911 | 0.034* | 0.46 (1) |
H14f | 0.4110 | 0.9314 | 0.5659 | 0.034* | 0.46 (1) |
H17 | 0.6400 | 1.0152 | 0.8610 | 0.019* | |
H18 | 0.8911 | 0.9832 | 0.8492 | 0.021* | |
H19 | 0.9999 | 0.5885 | 0.7565 | 0.021* | |
H20 | 0.7522 | 0.6102 | 0.7610 | 0.019* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0069 (1) | 0.0133 (1) | 0.0187 (1) | −0.0031 (1) | −0.0044 (1) | −0.0015 (1) |
O1 | 0.008 (1) | 0.018 (1) | 0.025 (1) | −0.005 (1) | −0.004 (1) | −0.004 (1) |
O2 | 0.011 (1) | 0.018 (1) | 0.031 (1) | −0.003 (1) | −0.004 (1) | −0.006 (1) |
N1 | 0.010 (1) | 0.017 (1) | 0.023 (1) | −0.005 (1) | −0.005 (1) | −0.003 (1) |
C1 | 0.007 (1) | 0.018 (1) | 0.020 (1) | −0.004 (1) | −0.004 (1) | −0.001 (1) |
C2 | 0.013 (1) | 0.018 (1) | 0.021 (1) | −0.005 (1) | −0.006 (1) | 0.000 (1) |
C3 | 0.015 (1) | 0.027 (2) | 0.024 (1) | −0.008 (1) | −0.003 (1) | −0.008 (1) |
C4 | 0.014 (1) | 0.017 (1) | 0.035 (2) | −0.004 (1) | −0.005 (1) | −0.008 (1) |
C5 | 0.013 (1) | 0.017 (1) | 0.030 (1) | −0.005 (1) | −0.005 (1) | 0.001 (1) |
C6 | 0.010 (1) | 0.020 (1) | 0.020 (1) | −0.004 (1) | −0.004 (1) | −0.001 (1) |
C7 | 0.010 (1) | 0.015 (1) | 0.022 (1) | −0.003 (1) | −0.004 (1) | −0.003 (1) |
C8 | 0.011 (1) | 0.022 (1) | 0.023 (1) | −0.006 (1) | −0.005 (1) | −0.002 (1) |
C9 | 0.017 (1) | 0.027 (2) | 0.025 (1) | −0.008 (1) | −0.008 (1) | −0.002 (1) |
C10 | 0.020 (1) | 0.023 (1) | 0.018 (1) | −0.006 (1) | −0.004 (1) | −0.002 (1) |
C11 | 0.011 (1) | 0.023 (1) | 0.025 (1) | −0.003 (1) | −0.001 (1) | −0.003 (1) |
C12 | 0.010 (1) | 0.023 (1) | 0.025 (1) | −0.003 (1) | −0.006 (1) | −0.003 (1) |
C13 | 0.026 (2) | 0.023 (2) | 0.032 (2) | −0.011 (1) | −0.016 (1) | 0.004 (1) |
C14 | 0.052 (4) | 0.048 (4) | 0.033 (3) | −0.027 (3) | −0.021 (3) | 0.010 (3) |
C14' | 0.020 (3) | 0.024 (3) | 0.020 (3) | −0.007 (2) | 0.000 (2) | 0.001 (2) |
C15 | 0.009 (1) | 0.015 (1) | 0.019 (1) | −0.004 (1) | −0.005 (1) | 0.000 (1) |
C16 | 0.008 (1) | 0.015 (1) | 0.016 (1) | −0.004 (1) | −0.004 (1) | 0.000 (1) |
C17 | 0.010 (1) | 0.016 (1) | 0.022 (1) | −0.003 (1) | −0.005 (1) | −0.004 (1) |
C18 | 0.012 (1) | 0.018 (1) | 0.026 (1) | −0.006 (1) | −0.006 (1) | −0.005 (1) |
C19 | 0.008 (1) | 0.017 (1) | 0.029 (1) | −0.003 (1) | −0.004 (1) | −0.005 (1) |
C20 | 0.0105 (1) | 0.015 (1) | 0.025 (1) | −0.005 (1) | −0.004 (1) | −0.005 (1) |
Sn1—C1 | 2.155 (3) | C17—C18 | 1.404 (3) |
Sn1—C7 | 2.186 (3) | C19—C20 | 1.408 (4) |
Sn1—C13 | 2.168 (3) | C2—H2 | 0.95 |
Sn1—N1i | 2.546 (2) | C3—H3 | 0.95 |
Sn1—O1 | 2.212 (2) | C4—H4 | 0.95 |
C15—O1 | 1.313 (3) | C5—H5 | 0.95 |
C15—O2 | 1.243 (3) | C6—H6 | 0.95 |
N1—C19 | 1.357 (4) | C8—H8 | 0.95 |
N1—C18 | 1.363 (4) | C9—H9 | 0.95 |
C1—C2 | 1.420 (4) | C10—H10 | 0.95 |
C1—C6 | 1.422 (4) | C11—H11 | 0.95 |
C2—C3 | 1.409 (4) | C12—H12 | 0.95 |
C3—C4 | 1.408 (4) | C13—H13a | 0.99 |
C4—C5 | 1.410 (4) | C13—H13b | 0.99 |
C5—C6 | 1.406 (4) | C13—H13c | 0.99 |
C7—C12 | 1.420 (4) | C13—H13d | 0.99 |
C7—C8 | 1.422 (4) | C14—H14a | 0.98 |
C8—C9 | 1.410 (4) | C14—H14b | 0.98 |
C9—C10 | 1.412 (4) | C14—H14c | 0.98 |
C10—C11 | 1.398 (4) | C14'—H14d | 0.98 |
C11—C12 | 1.414 (4) | C14'—H14e | 0.98 |
C13—C14' | 1.465 (6) | C14'—H14f | 0.98 |
C13—C14 | 1.527 (6) | C17—H17 | 0.95 |
C15—C16 | 1.535 (3) | C18—H18 | 0.95 |
C16—C20 | 1.407 (4) | C19—H19 | 0.95 |
C16—C17 | 1.410 (4) | C20—H20 | 0.95 |
C1—Sn1—C7 | 107.9 (1) | C5—C4—H4 | 120.0 |
C1—Sn1—C13 | 120.8 (1) | C6—C5—H5 | 120.0 |
C1—Sn1—O1 | 89.3 (1) | C4—C5—H5 | 120.0 |
C1—Sn1—N1i | 88.2 (1) | C5—C6—H6 | 119.4 |
C7—Sn1—C13 | 130.5 (1) | C1—C6—H6 | 119.4 |
C7—Sn1—O1 | 95.5 (1) | C9—C8—H8 | 119.4 |
C7—Sn1—N1i | 89.1 (1) | C7—C8—H8 | 119.4 |
C13—Sn1—O1 | 93.6 (1) | C8—C9—H9 | 120.0 |
C13—Sn1—N1i | 84.2 (1) | C10—C9—H9 | 120.0 |
N1i—Sn1—O1 | 175.3 (1) | C11—C10—H10 | 120.2 |
C15—O1—Sn1 | 114.5 (2) | C9—C10—H10 | 120.2 |
C19—N1—C18 | 117.8 (2) | C10—C11—H11 | 119.8 |
C19—N1—Sn1ii | 121.9 (2) | C12—C11—H11 | 119.8 |
C18—N1—Sn1ii | 120.3 (2) | C11—C12—H12 | 119.4 |
C2—C1—C6 | 117.6 (2) | C7—C12—H12 | 119.4 |
C2—C1—Sn1 | 123.6 (2) | C14—C13—H13a | 107.4 |
C6—C1—Sn1 | 118.8 (2) | Sn1—C13—H13a | 107.4 |
C3—C2—C1 | 121.7 (2) | C14—C13—H13b | 107.4 |
C4—C3—C2 | 119.5 (3) | Sn1—C13—H13b | 107.4 |
C3—C4—C5 | 120.1 (3) | H13a—C13—H13b | 106.9 |
C6—C5—C4 | 120.0 (3) | C14'—C13—H13c | 107.7 |
C5—C6—C1 | 121.2 (3) | Sn1—C13—H13c | 107.7 |
C12—C7—C8 | 117.5 (2) | C14'—C13—H13d | 107.7 |
C12—C7—Sn1 | 123.7 (2) | C14—C13—H13d | 127.5 |
C8—C7—Sn1 | 118.6 (2) | Sn1—C13—H13d | 107.7 |
C9—C8—C7 | 121.3 (2) | H13c—C13—H13d | 107.1 |
C8—C9—C10 | 120.1 (3) | C13—C14—H14a | 109.5 |
C11—C10—C9 | 119.6 (3) | C13—C14—H14b | 109.5 |
C10—C11—C12 | 120.4 (2) | H14a—C14—H14b | 109.5 |
C11—C12—C7 | 121.2 (2) | C13—C14—H14c | 109.5 |
C14'—C13—Sn1 | 118.3 (3) | H14a—C14—H14c | 109.5 |
C14—C13—Sn1 | 119.8 (3) | H14b—C14—H14c | 109.5 |
O2—C15—O1 | 125.0 (2) | C13—C14'—H14d | 109.5 |
O2—C15—C16 | 120.1 (2) | C13—C14'—H14e | 109.5 |
O1—C15—C16 | 114.9 (2) | H14d—C14'—H14e | 109.5 |
C20—C16—C17 | 118.6 (2) | C13—C14'—H14f | 109.5 |
C20—C16—C15 | 121.7 (2) | H14d—C14'—H14f | 109.5 |
C17—C16—C15 | 119.7 (2) | H14e—C14'—H14f | 109.5 |
C18—C17—C16 | 118.7 (2) | C18—C17—H17 | 120.6 |
N1—C18—C17 | 123.1 (2) | C16—C17—H17 | 120.6 |
N1—C19—C20 | 122.9 (2) | N1—C18—H18 | 118.5 |
C16—C20—C19 | 118.9 (2) | C17—C18—H18 | 118.5 |
C3—C2—H2 | 119.2 | N1—C19—H19 | 118.6 |
C1—C2—H2 | 119.2 | C20—C19—H19 | 118.6 |
C4—C3—H3 | 120.3 | C16—C20—H20 | 120.5 |
C2—C3—H3 | 120.3 | C19—C20—H20 | 120.5 |
C3—C4—H4 | 120.0 | ||
C1—Sn1—O1—C15 | −179.6 (2) | C8—C9—C10—C11 | 0.7 (4) |
C13—Sn1—O1—C15 | 59.6 (2) | C9—C10—C11—C12 | −1.1 (4) |
C7—Sn1—O1—C15 | −71.6 (2) | C10—C11—C12—C7 | 0.4 (4) |
C13—Sn1—C1—C2 | 5.9 (2) | C8—C7—C12—C11 | 0.7 (4) |
C7—Sn1—C1—C2 | 176.6 (2) | Sn1—C7—C12—C11 | 175.7 (2) |
O1—Sn1—C1—C2 | −87.8 (2) | C1—Sn1—C13—C14' | −48.2 (4) |
N1i—Sn1—C1—C2 | 88.1 (2) | C7—Sn1—C13—C14' | 143.5 (3) |
C13—Sn1—C1—C6 | −175.0 (2) | O1—Sn1—C13—C14' | 43.2 (4) |
C7—Sn1—C1—C6 | −4.3 (2) | N1i—Sn1—C13—C14' | −132.7 (4) |
O1—Sn1—C1—C6 | 91.3 (2) | C1—Sn1—C13—C14 | 32.3 (5) |
N1i—Sn1—C1—C6 | −92.8 (2) | C7—Sn1—C13—C14 | −135.9 (4) |
C6—C1—C2—C3 | −1.2 (4) | O1—Sn1—C13—C14 | 123.7 (4) |
Sn1—C1—C2—C3 | 177.9 (2) | N1i—Sn1—C13—C14 | −52.1 (4) |
C1—C2—C3—C4 | 0.5 (4) | Sn1—O1—C15—O2 | 2.7 (3) |
C2—C3—C4—C5 | 0.0 (4) | Sn1—O1—C15—C16 | −178.6 (2) |
C3—C4—C5—C6 | 0.2 (4) | O2—C15—C16—C20 | 173.0 (3) |
C4—C5—C6—C1 | −0.9 (4) | O1—C15—C16—C20 | −5.7 (4) |
C2—C1—C6—C5 | 1.4 (4) | O2—C15—C16—C17 | −3.9 (4) |
Sn1—C1—C6—C5 | −177.8 (2) | O1—C15—C16—C17 | 177.3 (2) |
C1—Sn1—C7—C12 | −87.2 (2) | C20—C16—C17—C18 | −0.1 (4) |
C13—Sn1—C7—C12 | 82.2 (3) | C15—C16—C17—C18 | 176.9 (2) |
O1—Sn1—C7—C12 | −178.3 (2) | C19—N1—C18—C17 | 2.0 (4) |
N1i—Sn1—C7—C12 | 0.6 (2) | Sn1ii—N1—C18—C17 | −176.8 (2) |
C1—Sn1—C7—C8 | 87.6 (2) | C16—C17—C18—N1 | −1.3 (4) |
C13—Sn1—C7—C8 | −102.9 (2) | C18—N1—C19—C20 | −1.3 (4) |
O1—Sn1—C7—C8 | −3.4 (2) | Sn1ii—N1—C19—C20 | 177.5 (2) |
N1i—Sn1—C7—C8 | 175.5 (2) | C17—C16—C20—C19 | 0.8 (4) |
C12—C7—C8—C9 | −1.1 (4) | C15—C16—C20—C19 | −176.2 (2) |
Sn1—C7—C8—C9 | −176.3 (2) | N1—C19—C20—C16 | −0.1 (4) |
C7—C8—C9—C10 | 0.4 (4) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |