Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044333/lh2206sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044333/lh2206Isup2.hkl |
CCDC reference: 275872
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.009 Å
- R factor = 0.036
- wR factor = 0.103
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.57 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C13
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.13 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.57 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 37.00 A 3
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
[Sn(C4H9)2(C12H13NO3)] | F(000) = 928 |
Mr = 452.15 | Dx = 1.347 Mg m−3 |
Monoclinic, P21/c | Melting point = 447–448 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.561 (5) Å | Cell parameters from 4579 reflections |
b = 10.827 (3) Å | θ = 2.3–25.2° |
c = 13.813 (4) Å | µ = 1.16 mm−1 |
β = 106.609 (4)° | T = 273 K |
V = 2229.9 (12) Å3 | Block, yellow |
Z = 4 | 0.43 × 0.37 × 0.29 mm |
Bruker SMART CCD diffractometer | 3919 independent reflections |
Radiation source: fine-focus sealed tube | 2887 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
Tmin = 0.622, Tmax = 0.715 | k = −12→7 |
11074 measured reflections | l = −16→16 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.214P] where P = (Fo2 + 2Fc2)/3 |
3919 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.98 e Å−3 |
24 restraints | Δρmin = −0.46 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.281913 (18) | 0.03789 (3) | 0.59287 (2) | 0.04640 (13) | |
N1 | 0.1586 (2) | 0.0969 (3) | 0.6221 (2) | 0.0390 (7) | |
O1 | 0.2013 (2) | −0.1275 (3) | 0.5785 (2) | 0.0562 (8) | |
O2 | 0.0582 (2) | −0.1848 (3) | 0.5380 (3) | 0.0749 (10) | |
O3 | 0.3155 (2) | 0.2260 (3) | 0.6182 (3) | 0.0710 (10) | |
C1 | 0.1193 (3) | −0.1150 (4) | 0.5791 (3) | 0.0513 (11) | |
C2 | 0.1020 (3) | −0.0047 (4) | 0.6378 (3) | 0.0450 (10) | |
H2 | 0.0389 | 0.0195 | 0.6119 | 0.054* | |
C3 | 0.1238 (4) | −0.0336 (4) | 0.7526 (4) | 0.0587 (12) | |
H3 | 0.1888 | −0.0448 | 0.7789 | 0.070* | |
C4 | 0.0795 (4) | −0.1520 (5) | 0.7715 (4) | 0.0865 (18) | |
H4A | 0.0974 | −0.2186 | 0.7357 | 0.130* | |
H4B | 0.0155 | −0.1426 | 0.7483 | 0.130* | |
H4C | 0.0974 | −0.1698 | 0.8425 | 0.130* | |
C5 | 0.0975 (6) | 0.0743 (6) | 0.8094 (4) | 0.103 (2) | |
H5A | 0.1262 | 0.1483 | 0.7962 | 0.155* | |
H5B | 0.1162 | 0.0574 | 0.8806 | 0.155* | |
H5C | 0.0336 | 0.0851 | 0.7872 | 0.155* | |
C6 | 0.1263 (3) | 0.2082 (4) | 0.6119 (3) | 0.0458 (10) | |
H6 | 0.0672 | 0.2168 | 0.6135 | 0.055* | |
C7 | 0.1717 (3) | 0.3192 (4) | 0.5985 (3) | 0.0481 (10) | |
C8 | 0.2616 (4) | 0.3244 (5) | 0.6013 (3) | 0.0594 (13) | |
C9 | 0.2983 (4) | 0.4398 (5) | 0.5884 (4) | 0.0819 (18) | |
H9 | 0.3579 | 0.4449 | 0.5885 | 0.098* | |
C10 | 0.2470 (6) | 0.5448 (5) | 0.5757 (5) | 0.094 (2) | |
H10 | 0.2726 | 0.6202 | 0.5674 | 0.112* | |
C11 | 0.1587 (6) | 0.5408 (5) | 0.5750 (4) | 0.087 (2) | |
H11 | 0.1253 | 0.6132 | 0.5679 | 0.104* | |
C12 | 0.1203 (4) | 0.4301 (4) | 0.5847 (3) | 0.0650 (14) | |
H12 | 0.0600 | 0.4270 | 0.5824 | 0.078* | |
C13 | 0.3948 (3) | −0.0208 (5) | 0.7159 (4) | 0.0712 (15) | |
C14 | 0.3923 (6) | −0.1551 (7) | 0.7316 (7) | 0.161 (4) | |
H14A | 0.3398 | −0.1757 | 0.7516 | 0.193* | |
H14B | 0.4449 | −0.1799 | 0.7836 | 0.193* | |
H14C | 0.3905 | −0.1973 | 0.6699 | 0.193* | |
C15 | 0.4769 (4) | 0.0125 (8) | 0.6855 (7) | 0.140 (3) | |
H15A | 0.4790 | 0.1003 | 0.6771 | 0.168* | |
H15B | 0.4750 | −0.0277 | 0.6230 | 0.168* | |
H15C | 0.5294 | −0.0139 | 0.7370 | 0.168* | |
C16 | 0.3963 (5) | 0.0457 (8) | 0.8102 (5) | 0.132 (3) | |
H16A | 0.3975 | 0.1331 | 0.7991 | 0.158* | |
H16B | 0.4487 | 0.0220 | 0.8629 | 0.158* | |
H16C | 0.3436 | 0.0250 | 0.8298 | 0.158* | |
C17 | 0.2711 (4) | 0.0346 (5) | 0.4329 (4) | 0.0700 (15) | |
C18 | 0.3248 (5) | 0.1385 (7) | 0.4045 (5) | 0.121 (3) | |
H18A | 0.3873 | 0.1276 | 0.4393 | 0.145* | |
H18B | 0.3048 | 0.2163 | 0.4235 | 0.145* | |
H18C | 0.3164 | 0.1374 | 0.3329 | 0.145* | |
C19 | 0.3053 (5) | −0.0878 (7) | 0.4057 (5) | 0.114 (2) | |
H19A | 0.3677 | −0.0965 | 0.4416 | 0.137* | |
H19B | 0.2979 | −0.0904 | 0.3344 | 0.137* | |
H19C | 0.2720 | −0.1540 | 0.4241 | 0.137* | |
C20 | 0.1727 (5) | 0.0508 (8) | 0.3757 (4) | 0.108 (3) | |
H20A | 0.1520 | 0.1291 | 0.3928 | 0.129* | |
H20B | 0.1383 | −0.0143 | 0.3938 | 0.129* | |
H20C | 0.1656 | 0.0478 | 0.3044 | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.04623 (19) | 0.03927 (19) | 0.0534 (2) | 0.00444 (14) | 0.01382 (13) | 0.00379 (14) |
N1 | 0.0442 (18) | 0.0302 (18) | 0.0415 (18) | 0.0020 (16) | 0.0104 (14) | 0.0021 (15) |
O1 | 0.062 (2) | 0.0350 (16) | 0.074 (2) | 0.0039 (15) | 0.0219 (16) | −0.0009 (15) |
O2 | 0.068 (2) | 0.0445 (19) | 0.095 (3) | −0.0107 (18) | −0.0045 (18) | −0.0056 (19) |
O3 | 0.0567 (18) | 0.046 (2) | 0.101 (3) | −0.0138 (17) | 0.0077 (17) | 0.0029 (19) |
C1 | 0.063 (3) | 0.032 (2) | 0.052 (3) | 0.001 (2) | 0.007 (2) | 0.005 (2) |
C2 | 0.042 (2) | 0.039 (2) | 0.053 (3) | 0.0008 (18) | 0.0114 (19) | 0.0064 (19) |
C3 | 0.068 (3) | 0.059 (3) | 0.051 (3) | 0.000 (3) | 0.019 (2) | 0.013 (2) |
C4 | 0.107 (4) | 0.074 (4) | 0.083 (4) | −0.011 (4) | 0.035 (3) | 0.025 (3) |
C5 | 0.186 (7) | 0.076 (4) | 0.068 (4) | 0.014 (5) | 0.067 (4) | 0.005 (3) |
C6 | 0.055 (2) | 0.039 (2) | 0.042 (2) | 0.011 (2) | 0.0122 (19) | 0.0019 (19) |
C7 | 0.070 (3) | 0.033 (2) | 0.037 (2) | 0.005 (2) | 0.009 (2) | −0.0020 (18) |
C8 | 0.080 (3) | 0.035 (3) | 0.053 (3) | −0.005 (2) | 0.003 (2) | 0.002 (2) |
C9 | 0.100 (4) | 0.046 (3) | 0.083 (4) | −0.022 (3) | 0.000 (3) | 0.005 (3) |
C10 | 0.152 (6) | 0.036 (3) | 0.072 (4) | −0.022 (4) | −0.001 (4) | 0.005 (3) |
C11 | 0.157 (7) | 0.030 (3) | 0.061 (3) | 0.012 (4) | 0.011 (4) | −0.004 (2) |
C12 | 0.108 (4) | 0.040 (3) | 0.044 (3) | 0.018 (3) | 0.018 (3) | 0.000 (2) |
C13 | 0.053 (3) | 0.067 (4) | 0.080 (4) | 0.010 (3) | −0.003 (3) | 0.008 (3) |
C14 | 0.143 (6) | 0.097 (5) | 0.182 (7) | 0.036 (5) | −0.050 (5) | 0.034 (5) |
C15 | 0.049 (3) | 0.216 (10) | 0.142 (7) | 0.014 (5) | 0.003 (4) | 0.028 (6) |
C16 | 0.104 (5) | 0.182 (10) | 0.080 (5) | 0.044 (6) | −0.019 (4) | −0.015 (5) |
C17 | 0.079 (4) | 0.080 (4) | 0.057 (3) | 0.004 (3) | 0.030 (3) | 0.000 (3) |
C18 | 0.152 (6) | 0.132 (7) | 0.104 (5) | −0.024 (6) | 0.079 (5) | 0.018 (5) |
C19 | 0.150 (6) | 0.115 (6) | 0.097 (5) | 0.016 (5) | 0.068 (5) | −0.018 (5) |
C20 | 0.102 (5) | 0.167 (8) | 0.048 (3) | 0.028 (5) | 0.011 (3) | 0.019 (4) |
Sn1—O3 | 2.107 (3) | C10—C11 | 1.372 (10) |
Sn1—C13 | 2.161 (5) | C10—H10 | 0.9300 |
Sn1—O1 | 2.163 (3) | C11—C12 | 1.363 (8) |
Sn1—N1 | 2.168 (3) | C11—H11 | 0.9300 |
Sn1—C17 | 2.168 (5) | C12—H12 | 0.9300 |
N1—C6 | 1.298 (5) | C13—C14 | 1.472 (9) |
N1—C2 | 1.462 (5) | C13—C16 | 1.484 (9) |
O1—C1 | 1.285 (5) | C13—C15 | 1.498 (9) |
O2—C1 | 1.220 (5) | C14—H14A | 0.9600 |
O3—C8 | 1.334 (6) | C14—H14B | 0.9600 |
C1—C2 | 1.510 (6) | C14—H14C | 0.9600 |
C2—C3 | 1.556 (6) | C15—H15A | 0.9600 |
C2—H2 | 0.9800 | C15—H15B | 0.9600 |
C3—C4 | 1.513 (7) | C15—H15C | 0.9600 |
C3—C5 | 1.527 (8) | C16—H16A | 0.9600 |
C3—H3 | 0.9800 | C16—H16B | 0.9600 |
C4—H4A | 0.9600 | C16—H16C | 0.9600 |
C4—H4B | 0.9600 | C17—C20 | 1.519 (9) |
C4—H4C | 0.9600 | C17—C19 | 1.515 (9) |
C5—H5A | 0.9600 | C17—C18 | 1.519 (8) |
C5—H5B | 0.9600 | C18—H18A | 0.9600 |
C5—H5C | 0.9600 | C18—H18B | 0.9600 |
C6—C7 | 1.433 (6) | C18—H18C | 0.9600 |
C6—H6 | 0.9300 | C19—H19A | 0.9600 |
C7—C8 | 1.390 (7) | C19—H19B | 0.9600 |
C7—C12 | 1.425 (6) | C19—H19C | 0.9600 |
C8—C9 | 1.406 (7) | C20—H20A | 0.9600 |
C9—C10 | 1.371 (9) | C20—H20B | 0.9600 |
C9—H9 | 0.9300 | C20—H20C | 0.9600 |
O3—Sn1—C13 | 92.66 (18) | C11—C10—H10 | 119.3 |
O3—Sn1—O1 | 157.70 (13) | C12—C11—C10 | 119.6 (6) |
C13—Sn1—O1 | 98.54 (17) | C12—C11—H11 | 120.2 |
O3—Sn1—N1 | 82.80 (13) | C10—C11—H11 | 120.2 |
C13—Sn1—N1 | 120.29 (18) | C11—C12—C7 | 120.6 (6) |
O1—Sn1—N1 | 74.90 (12) | C11—C12—H12 | 119.7 |
O3—Sn1—C17 | 97.39 (18) | C7—C12—H12 | 119.7 |
C13—Sn1—C17 | 127.3 (2) | C14—C13—C16 | 110.1 (6) |
O1—Sn1—C17 | 91.09 (17) | C14—C13—C15 | 109.9 (6) |
N1—Sn1—C17 | 112.31 (17) | C16—C13—C15 | 109.2 (6) |
C6—N1—C2 | 118.9 (3) | C14—C13—Sn1 | 110.9 (4) |
C6—N1—Sn1 | 126.1 (3) | C16—C13—Sn1 | 110.7 (4) |
C2—N1—Sn1 | 114.1 (3) | C15—C13—Sn1 | 106.0 (4) |
C1—O1—Sn1 | 117.6 (3) | C13—C14—H14A | 109.5 |
C8—O3—Sn1 | 129.0 (3) | C13—C14—H14B | 109.5 |
O2—C1—O1 | 125.1 (4) | H14A—C14—H14B | 109.5 |
O2—C1—C2 | 120.3 (4) | C13—C14—H14C | 109.5 |
O1—C1—C2 | 114.6 (4) | H14A—C14—H14C | 109.5 |
N1—C2—C1 | 108.0 (3) | H14B—C14—H14C | 109.5 |
N1—C2—C3 | 109.7 (3) | C13—C15—H15A | 109.5 |
C1—C2—C3 | 111.6 (4) | C13—C15—H15B | 109.5 |
N1—C2—H2 | 109.2 | H15A—C15—H15B | 109.5 |
C1—C2—H2 | 109.2 | C13—C15—H15C | 109.5 |
C3—C2—H2 | 109.2 | H15A—C15—H15C | 109.5 |
C4—C3—C5 | 110.9 (5) | H15B—C15—H15C | 109.5 |
C4—C3—C2 | 111.7 (4) | C13—C16—H16A | 109.5 |
C5—C3—C2 | 110.9 (4) | C13—C16—H16B | 109.5 |
C4—C3—H3 | 107.7 | H16A—C16—H16B | 109.5 |
C5—C3—H3 | 107.7 | C13—C16—H16C | 109.5 |
C2—C3—H3 | 107.7 | H16A—C16—H16C | 109.5 |
C3—C4—H4A | 109.5 | H16B—C16—H16C | 109.5 |
C3—C4—H4B | 109.5 | C20—C17—C19 | 110.2 (6) |
H4A—C4—H4B | 109.5 | C20—C17—C18 | 109.2 (6) |
C3—C4—H4C | 109.5 | C19—C17—C18 | 109.0 (5) |
H4A—C4—H4C | 109.5 | C20—C17—Sn1 | 107.6 (4) |
H4B—C4—H4C | 109.5 | C19—C17—Sn1 | 109.7 (4) |
C3—C5—H5A | 109.5 | C18—C17—Sn1 | 111.3 (4) |
C3—C5—H5B | 109.5 | C17—C18—H18A | 109.5 |
H5A—C5—H5B | 109.5 | C17—C18—H18B | 109.5 |
C3—C5—H5C | 109.5 | H18A—C18—H18B | 109.5 |
H5A—C5—H5C | 109.5 | C17—C18—H18C | 109.5 |
H5B—C5—H5C | 109.5 | H18A—C18—H18C | 109.5 |
N1—C6—C7 | 127.1 (4) | H18B—C18—H18C | 109.5 |
N1—C6—H6 | 116.5 | C17—C19—H19A | 109.5 |
C7—C6—H6 | 116.5 | C17—C19—H19B | 109.5 |
C8—C7—C12 | 119.5 (5) | H19A—C19—H19B | 109.5 |
C8—C7—C6 | 124.0 (4) | C17—C19—H19C | 109.5 |
C12—C7—C6 | 116.4 (4) | H19A—C19—H19C | 109.5 |
O3—C8—C7 | 123.4 (4) | H19B—C19—H19C | 109.5 |
O3—C8—C9 | 118.3 (5) | C17—C20—H20A | 109.5 |
C7—C8—C9 | 118.3 (5) | C17—C20—H20B | 109.5 |
C10—C9—C8 | 120.7 (7) | H20A—C20—H20B | 109.5 |
C10—C9—H9 | 119.6 | C17—C20—H20C | 109.5 |
C8—C9—H9 | 119.6 | H20A—C20—H20C | 109.5 |
C9—C10—C11 | 121.3 (6) | H20B—C20—H20C | 109.5 |
C9—C10—H10 | 119.3 |
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