metal-organic compounds
The six-coordinate Sn atom (site symmetry 2) in the monomeric title complex, [Sn(CH3)2(C6H4NO3)2], exists in a skew-trapezoidal geometry [C-Sn-C = 149.4 (3)°].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032277/hb6285sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032277/hb6285Isup2.hkl |
CCDC reference: 260188
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.034
- wR factor = 0.090
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.416 0.699 Tmin(prime) and Tmax expected: 0.464 0.680 RR(prime) = 0.873 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 6 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O3 -H3O 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.94(3), Rep 0.940(10) ...... 3.00 su-Rat C1 -H11 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.95(3), Rep 0.950(10) ...... 3.00 su-Rat C2 -H2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.95(3), Rep 0.950(10) ...... 3.00 su-Rat C4 -H4 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O3 -H3O 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis(3-hydroxypyridine-2-carboxylato)dimethyltin(IV) top
Crystal data top
[Sn(CH3)2(C6H4NO3)2] | F(000) = 840 |
Mr = 424.96 | Dx = 1.818 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3129 reflections |
a = 9.228 (1) Å | θ = 2.7–28.3° |
b = 13.363 (2) Å | µ = 1.68 mm−1 |
c = 13.222 (2) Å | T = 295 K |
β = 107.783 (1)° | Block, colorless |
V = 1552.5 (3) Å3 | 0.45 × 0.27 × 0.23 mm |
Z = 4 |
Data collection top
Bruker SMART area-detector diffractometer | 1783 independent reflections |
Radiation source: fine-focus sealed tube | 1605 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.416, Tmax = 0.699 | k = −11→17 |
4512 measured reflections | l = −14→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) = 0.090 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0461P)2 + 2.0757P] where P = (Fo2 + 2Fc2)/3 |
1783 reflections | (Δ/σ)max = 0.001 |
133 parameters | Δρmax = 1.25 e Å−3 |
10 restraints | Δρmin = −0.82 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.5000 | 0.31592 (2) | 0.7500 | 0.0353 (1) | |
O1 | 0.3843 (3) | 0.1928 (2) | 0.7912 (2) | 0.045 (1) | |
O2 | 0.2041 (4) | 0.1282 (2) | 0.8507 (2) | 0.054 (1) | |
O3 | 0.0206 (4) | 0.2426 (3) | 0.9105 (3) | 0.058 (1) | |
N1 | 0.2965 (3) | 0.3797 (2) | 0.8200 (2) | 0.036 (1) | |
C1 | 0.6480 (5) | 0.3574 (4) | 0.8992 (3) | 0.051 (1) | |
C2 | 0.2568 (5) | 0.4726 (3) | 0.8332 (3) | 0.043 (1) | |
C3 | 0.1368 (5) | 0.4939 (3) | 0.8724 (3) | 0.049 (1) | |
C4 | 0.0575 (4) | 0.4174 (3) | 0.8988 (3) | 0.046 (1) | |
C5 | 0.0983 (4) | 0.3187 (3) | 0.8857 (3) | 0.038 (1) | |
C6 | 0.2198 (4) | 0.3036 (2) | 0.8456 (2) | 0.032 (1) | |
C7 | 0.2714 (4) | 0.2009 (3) | 0.8285 (3) | 0.038 (1) | |
H3o | 0.061 (6) | 0.189 (2) | 0.898 (5) | 0.07 (2)* | |
H2 | 0.311 (4) | 0.525 (2) | 0.813 (3) | 0.05 (1)* | |
H3 | 0.111 (4) | 0.562 (1) | 0.878 (3) | 0.04 (1)* | |
H4 | −0.029 (3) | 0.430 (3) | 0.922 (3) | 0.05 (1)* | |
H11 | 0.605 (4) | 0.340 (3) | 0.953 (2) | 0.06 (1)* | |
H12 | 0.661 (4) | 0.428 (1) | 0.897 (4) | 0.09 (2)* | |
H13 | 0.743 (2) | 0.325 (2) | 0.911 (3) | 0.05 (1)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0377 (2) | 0.0309 (2) | 0.0399 (2) | 0.000 | 0.0158 (1) | 0.000 |
O1 | 0.050 (2) | 0.029 (1) | 0.066 (2) | 0.006 (1) | 0.031 (1) | 0.000 (1) |
O2 | 0.067 (2) | 0.037 (2) | 0.069 (2) | −0.008 (1) | 0.037 (2) | 0.002 (1) |
O3 | 0.056 (2) | 0.063 (2) | 0.069 (2) | −0.009 (2) | 0.040 (2) | 0.000 (2) |
N1 | 0.037 (1) | 0.035 (2) | 0.037 (1) | 0.003 (12) | 0.014 (1) | 0.003 (1) |
C1 | 0.048 (2) | 0.066 (3) | 0.036 (2) | −0.002 (2) | 0.012 (2) | 0.001 (2) |
C2 | 0.052 (2) | 0.035 (2) | 0.042 (2) | 0.001 (2) | 0.014 (2) | 0.003 (2) |
C3 | 0.056 (2) | 0.045 (2) | 0.042 (2) | 0.016 (2) | 0.010 (2) | −0.006 (2) |
C4 | 0.041 (2) | 0.061 (3) | 0.039 (2) | 0.012 (2) | 0.014 (2) | −0.008 (2) |
C5 | 0.037 (2) | 0.051 (2) | 0.028 (2) | −0.001 (2) | 0.010 (1) | −0.002 (1) |
C6 | 0.030 (2) | 0.038 (2) | 0.025 (1) | 0.001 (1) | 0.007 (1) | −0.001 (1) |
C7 | 0.042 (2) | 0.036 (2) | 0.039 (2) | −0.003 (1) | 0.018 (2) | 0.000 (1) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.102 (4) | C3—C4 | 1.363 (7) |
Sn1—C1i | 2.102 (4) | C4—C5 | 1.397 (6) |
Sn1—N1 | 2.485 (3) | C5—C6 | 1.394 (5) |
Sn1—N1i | 2.485 (3) | C6—C7 | 1.492 (5) |
Sn1—O1 | 2.120 (3) | O3—H3o | 0.85 (1) |
Sn1—O1i | 2.120 (3) | C1—H11 | 0.94 (1) |
O1—C7 | 1.286 (5) | C1—H12 | 0.95 (1) |
O2—C7 | 1.236 (4) | C1—H13 | 0.95 (1) |
O3—C5 | 1.341 (5) | C2—H2 | 0.95 (1) |
N1—C2 | 1.321 (5) | C3—H3 | 0.95 (1) |
N1—C6 | 1.340 (4) | C4—H4 | 0.95 (1) |
C2—C3 | 1.388 (6) | ||
C1—Sn1—C1i | 149.4 (3) | O3—C5—C6 | 122.3 (3) |
C1—Sn1—O1 | 101.4 (2) | O3—C5—C4 | 120.0 (3) |
C1—Sn1—O1i | 102.2 (2) | C6—C5—C4 | 117.6 (3) |
C1—Sn1—N1 | 84.7 (1) | N1—C6—C5 | 122.3 (3) |
C1—Sn1—N1i | 84.9 (1) | N1—C6—C7 | 116.3 (3) |
C1i—Sn1—O1 | 102.2 (2) | C5—C6—C7 | 121.5 (3) |
C1i—Sn1—O1i | 101.4 (2) | O2—C7—O1 | 123.3 (3) |
C1i—Sn1—N1i | 84.7 (1) | O2—C7—C6 | 118.7 (3) |
C1i—Sn1—N1 | 84.9 (1) | O1—C7—C6 | 117.9 (3) |
N1—Sn1—N1i | 139.9 (1) | C5—O3—H3o | 107 (4) |
N1—Sn1—O1 | 70.9 (1) | Sn1—C1—H11 | 110 (3) |
N1—Sn1—O1i | 149.2 (1) | Sn1—C1—H12 | 106 (3) |
N1i—Sn1—O1 | 149.2 (1) | H11—C1—H12 | 111 (2) |
N1i—Sn1—O1i | 70.9 (1) | Sn1—C1—H13 | 110 (3) |
O1—Sn1—O1i | 78.3 (1) | H11—C1—H13 | 110 (2) |
C7—O1—Sn1 | 124.3 (2) | H12—C1—H13 | 110 (2) |
C2—N1—C6 | 119.4 (3) | N1—C2—H2 | 118 (3) |
C2—N1—Sn1 | 130.0 (3) | C3—C2—H2 | 120 (3) |
C6—N1—Sn1 | 110.6 (2) | C4—C3—H3 | 122 (2) |
N1—C2—C3 | 121.8 (4) | C2—C3—H3 | 118 (2) |
C4—C3—C2 | 119.6 (4) | C3—C4—H4 | 121 (3) |
C3—C4—C5 | 119.3 (3) | C5—C4—H4 | 119 (3) |
C1—Sn1—O1—C7 | 81.3 (3) | C2—C3—C4—C5 | −0.2 (6) |
C1i—Sn1—O1—C7 | −79.1 (3) | C3—C4—C5—O3 | −179.4 (3) |
O1i—Sn1—O1—C7 | −178.4 (4) | C3—C4—C5—C6 | 0.0 (5) |
N1i—Sn1—O1—C7 | −179.5 (2) | C2—N1—C6—C5 | 0.2 (5) |
N1—Sn1—O1—C7 | 1.0 (3) | Sn1—N1—C6—C5 | −179.2 (2) |
C1—Sn1—N1—C2 | 75.9 (3) | C2—N1—C6—C7 | 180.0 (3) |
C1i—Sn1—N1—C2 | −75.3 (3) | Sn1—N1—C6—C7 | 0.6 (3) |
O1—Sn1—N1—C2 | 179.9 (3) | O3—C5—C6—N1 | 179.4 (3) |
O1i—Sn1—N1—C2 | −179.0 (3) | C4—C5—C6—N1 | −0.1 (5) |
N1i—Sn1—N1—C2 | 0.3 (3) | O3—C5—C6—C7 | −0.4 (5) |
C1—Sn1—N1—C6 | −104.7 (2) | C4—C5—C6—C7 | −179.8 (3) |
C1i—Sn1—N1—C6 | 104.1 (3) | Sn1—O1—C7—O2 | 179.0 (3) |
O1—Sn1—N1—C6 | −0.8 (2) | Sn1—O1—C7—C6 | −1.1 (5) |
O1i—Sn1—N1—C6 | 0.4 (3) | N1—C6—C7—O2 | −179.9 (3) |
N1i—Sn1—N1—C6 | 179.6 (2) | C5—C6—C7—O2 | −0.1 (5) |
C6—N1—C2—C3 | −0.4 (5) | N1—C6—C7—O1 | 0.2 (5) |
Sn1—N1—C2—C3 | 178.9 (3) | C5—C6—C7—O1 | 180.0 (3) |
N1—C2—C3—C4 | 0.4 (6) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3o···O2 | 0.85 (1) | 1.82 (3) | 2.578 (5) | 149 (6) |