Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054980/lh2542sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054980/lh2542Isup2.hkl |
CCDC reference: 635601
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.046
- wR factor = 0.123
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Aizawa et al. (1996); Dubey & Roy (2003); Ma et al. (2005).
The reaction was carried out under N2 atmoshpere. 2,6-pyridinedicarboxylic acid (0.167 g, 1 mmol) was added to a solution of benzene(30 ml) with sodium ethoxide (0.136 g, 2 mmol)in a Schlenk flask. After stirring for 10 min, dimethyltin dichloride (0.220 g, 1 mmol) was added to the mixture. The mixture was kept at 313 K for 12 h. After cooling to room temperature, the solution was filtered. The solvent of the filtrate was gradually removed by evaporation under vacuum until a solid product was obtained. The solid was then recrystallized from diethyl ether. Colorless single crystals of the title complex were obtained after one week. Yield, 81%. Analysis calculated for C18H22N2O10Sn2: C 32.57, H 3.34, N, 4.22; found: C 32.36, H 3.22, N, 4.31. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.
All H atoms were placed geometrically idealized positions and treated as riding on their parent atoms, with aromatic C—H distances of 0.93 Å and methyl C—H distances of 0.96 Å. The Uiso(H) values were set at 1.2Ueq(C) for the aromatic H atoms and 1.5Ueq(C) for methyl H atoms.
Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme for non-H atoms [symmetry code: (A) 1 - x, -y, 1 - z]. |
[Sn2(CH3)4(C7H3NO4)2(H2O)2] | F(000) = 1296 |
Mr = 663.76 | Dx = 1.940 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2820 reflections |
a = 11.319 (5) Å | θ = 2.6–28.2° |
b = 10.705 (4) Å | µ = 2.25 mm−1 |
c = 18.768 (8) Å | T = 298 K |
β = 91.864 (5)° | Block, colorless |
V = 2272.9 (16) Å3 | 0.23 × 0.17 × 0.14 mm |
Z = 4 |
Bruker SMART CCD area detector diffractometer | 1998 independent reflections |
Radiation source: fine-focus sealed tube | 1645 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.625, Tmax = 0.743 | k = −12→12 |
5571 measured reflections | l = −19→22 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.077P)2] where P = (Fo2 + 2Fc2)/3 |
1998 reflections | (Δ/σ)max < 0.001 |
147 parameters | Δρmax = 0.99 e Å−3 |
4 restraints | Δρmin = −1.94 e Å−3 |
[Sn2(CH3)4(C7H3NO4)2(H2O)2] | V = 2272.9 (16) Å3 |
Mr = 663.76 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.319 (5) Å | µ = 2.25 mm−1 |
b = 10.705 (4) Å | T = 298 K |
c = 18.768 (8) Å | 0.23 × 0.17 × 0.14 mm |
β = 91.864 (5)° |
Bruker SMART CCD area detector diffractometer | 1998 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1645 reflections with I > 2σ(I) |
Tmin = 0.625, Tmax = 0.743 | Rint = 0.059 |
5571 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 4 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.99 e Å−3 |
1998 reflections | Δρmin = −1.94 e Å−3 |
147 parameters |
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 | 0.39712 (4) | 0.01350 (4) | 0.59215 (2) | 0.0274 (2) | |
N1 | 0.4229 (4) | 0.2188 (4) | 0.6236 (3) | 0.0236 (11) | |
O1 | 0.5332 (4) | 0.1262 (4) | 0.5141 (2) | 0.0270 (10) | |
O2 | 0.5885 (5) | 0.3132 (4) | 0.4773 (3) | 0.0440 (13) | |
O3 | 0.2964 (5) | 0.0520 (5) | 0.6883 (3) | 0.0435 (12) | |
O4 | 0.2345 (6) | 0.1879 (5) | 0.7685 (3) | 0.0642 (18) | |
O5 | 0.2951 (4) | −0.1711 (4) | 0.6116 (3) | 0.0415 (12) | |
H1 | 0.2831 | −0.1981 | 0.6534 | 0.062* | |
H2 | 0.3360 | −0.2263 | 0.5911 | 0.062* | |
C1 | 0.5411 (5) | 0.2409 (6) | 0.5194 (3) | 0.0261 (14) | |
C2 | 0.4850 (5) | 0.2990 (6) | 0.5842 (3) | 0.0255 (14) | |
C3 | 0.4904 (5) | 0.4248 (6) | 0.6008 (4) | 0.0329 (15) | |
H3 | 0.5341 | 0.4793 | 0.5735 | 0.039* | |
C4 | 0.4294 (7) | 0.4685 (7) | 0.6589 (4) | 0.0393 (17) | |
H4 | 0.4324 | 0.5527 | 0.6711 | 0.047* | |
C5 | 0.3639 (6) | 0.3850 (6) | 0.6986 (4) | 0.0315 (15) | |
H5A | 0.3221 | 0.4127 | 0.7374 | 0.038* | |
C6 | 0.3620 (5) | 0.2609 (6) | 0.6794 (3) | 0.0290 (14) | |
C7 | 0.2929 (6) | 0.1611 (6) | 0.7156 (4) | 0.0373 (17) | |
C8 | 0.2604 (5) | 0.0637 (7) | 0.5183 (4) | 0.0348 (16) | |
H8A | 0.2927 | 0.1119 | 0.4804 | 0.052* | |
H8B | 0.2022 | 0.1124 | 0.5419 | 0.052* | |
H8C | 0.2241 | −0.0105 | 0.4989 | 0.052* | |
C9 | 0.5481 (6) | −0.0590 (8) | 0.6463 (4) | 0.0439 (18) | |
H9A | 0.5806 | −0.1257 | 0.6188 | 0.066* | |
H9B | 0.5265 | −0.0904 | 0.6920 | 0.066* | |
H9C | 0.6060 | 0.0059 | 0.6527 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0322 (3) | 0.0288 (3) | 0.0212 (3) | −0.00140 (17) | 0.0044 (2) | −0.00003 (18) |
N1 | 0.026 (3) | 0.029 (3) | 0.016 (3) | 0.000 (2) | 0.003 (2) | 0.000 (2) |
O1 | 0.034 (2) | 0.029 (3) | 0.018 (2) | −0.0059 (18) | 0.0012 (19) | −0.0028 (18) |
O2 | 0.063 (3) | 0.032 (3) | 0.038 (3) | −0.013 (2) | 0.027 (3) | −0.005 (2) |
O3 | 0.062 (3) | 0.039 (3) | 0.030 (3) | −0.009 (3) | 0.023 (2) | −0.004 (2) |
O4 | 0.104 (5) | 0.049 (3) | 0.043 (4) | −0.015 (3) | 0.048 (3) | −0.011 (3) |
O5 | 0.062 (3) | 0.030 (3) | 0.034 (3) | −0.001 (2) | 0.019 (2) | 0.001 (2) |
C1 | 0.028 (3) | 0.028 (4) | 0.022 (3) | −0.004 (3) | 0.001 (3) | 0.001 (3) |
C2 | 0.020 (3) | 0.034 (4) | 0.022 (4) | 0.000 (2) | 0.000 (3) | 0.000 (3) |
C3 | 0.031 (3) | 0.034 (4) | 0.034 (4) | −0.006 (3) | 0.007 (3) | −0.001 (3) |
C4 | 0.048 (4) | 0.031 (4) | 0.039 (5) | −0.002 (3) | 0.007 (4) | −0.009 (3) |
C5 | 0.032 (4) | 0.038 (4) | 0.025 (4) | 0.004 (3) | 0.003 (3) | −0.007 (3) |
C6 | 0.032 (3) | 0.033 (4) | 0.022 (3) | −0.003 (3) | 0.002 (3) | 0.000 (3) |
C7 | 0.050 (4) | 0.032 (4) | 0.031 (4) | −0.004 (3) | 0.011 (3) | −0.006 (3) |
C8 | 0.030 (3) | 0.036 (4) | 0.039 (4) | −0.004 (3) | 0.003 (3) | 0.006 (3) |
C9 | 0.045 (4) | 0.064 (5) | 0.023 (4) | 0.007 (4) | −0.005 (3) | 0.002 (4) |
Sn1—C9 | 2.108 (7) | C1—C2 | 1.523 (8) |
Sn1—C8 | 2.114 (6) | C2—C3 | 1.383 (9) |
Sn1—O3 | 2.204 (5) | C3—C4 | 1.390 (10) |
Sn1—N1 | 2.292 (5) | C3—H3 | 0.9300 |
Sn1—O5 | 2.324 (5) | C4—C5 | 1.394 (10) |
Sn1—O1 | 2.473 (4) | C4—H4 | 0.9300 |
Sn1—O1i | 2.634 (5) | C5—C6 | 1.376 (9) |
N1—C2 | 1.347 (7) | C5—H5A | 0.9300 |
N1—C6 | 1.350 (8) | C6—C7 | 1.499 (9) |
O1—C1 | 1.235 (7) | C8—H8A | 0.9600 |
O2—C1 | 1.241 (7) | C8—H8B | 0.9600 |
O3—C7 | 1.277 (8) | C8—H8C | 0.9600 |
O4—C7 | 1.245 (8) | C9—H9A | 0.9600 |
O5—H1 | 0.8500 | C9—H9B | 0.9600 |
O5—H2 | 0.8500 | C9—H9C | 0.9600 |
C9—Sn1—C8 | 167.1 (3) | C3—C2—C1 | 124.2 (6) |
C9—Sn1—O3 | 96.1 (2) | C2—C3—C4 | 119.1 (6) |
C8—Sn1—O3 | 95.9 (2) | C2—C3—H3 | 120.5 |
C9—Sn1—N1 | 97.7 (3) | C4—C3—H3 | 120.5 |
C8—Sn1—N1 | 90.6 (2) | C3—C4—C5 | 119.3 (6) |
O3—Sn1—N1 | 71.02 (17) | C3—C4—H4 | 120.3 |
C9—Sn1—O5 | 90.6 (3) | C5—C4—H4 | 120.3 |
C8—Sn1—O5 | 87.8 (2) | C6—C5—C4 | 118.9 (6) |
O3—Sn1—O5 | 75.95 (17) | C6—C5—H5A | 120.6 |
N1—Sn1—O5 | 146.58 (17) | C4—C5—H5A | 120.6 |
C9—Sn1—O1 | 87.4 (2) | N1—C6—C5 | 121.4 (6) |
C8—Sn1—O1 | 86.8 (2) | N1—C6—C7 | 113.5 (6) |
O3—Sn1—O1 | 137.91 (16) | C5—C6—C7 | 125.0 (6) |
N1—Sn1—O1 | 66.95 (15) | O4—C7—O3 | 123.7 (6) |
O5—Sn1—O1 | 146.11 (15) | O4—C7—C6 | 119.7 (6) |
C2—N1—C6 | 120.1 (5) | O3—C7—C6 | 116.6 (6) |
C2—N1—Sn1 | 122.3 (4) | Sn1—C8—H8A | 109.5 |
C6—N1—Sn1 | 117.2 (4) | Sn1—C8—H8B | 109.5 |
C1—O1—Sn1 | 118.9 (4) | H8A—C8—H8B | 109.5 |
C7—O3—Sn1 | 121.5 (4) | Sn1—C8—H8C | 109.5 |
Sn1—O5—H1 | 121.9 | H8A—C8—H8C | 109.5 |
Sn1—O5—H2 | 103.8 | H8B—C8—H8C | 109.5 |
H1—O5—H2 | 106.7 | Sn1—C9—H9A | 109.5 |
O1—C1—O2 | 126.9 (6) | Sn1—C9—H9B | 109.5 |
O1—C1—C2 | 116.0 (5) | H9A—C9—H9B | 109.5 |
O2—C1—C2 | 117.0 (6) | Sn1—C9—H9C | 109.5 |
N1—C2—C3 | 121.1 (6) | H9A—C9—H9C | 109.5 |
N1—C2—C1 | 114.7 (5) | H9B—C9—H9C | 109.5 |
C9—Sn1—N1—C2 | 89.9 (5) | Sn1—N1—C2—C3 | 174.1 (5) |
C8—Sn1—N1—C2 | −80.2 (5) | C6—N1—C2—C1 | −175.2 (5) |
O3—Sn1—N1—C2 | −176.3 (5) | Sn1—N1—C2—C1 | −2.8 (7) |
O5—Sn1—N1—C2 | −167.2 (4) | O1—C1—C2—N1 | −6.6 (8) |
O1—Sn1—N1—C2 | 6.1 (4) | O2—C1—C2—N1 | 172.5 (6) |
C9—Sn1—N1—C6 | −97.5 (5) | O1—C1—C2—C3 | 176.6 (6) |
C8—Sn1—N1—C6 | 92.5 (5) | O2—C1—C2—C3 | −4.3 (10) |
O3—Sn1—N1—C6 | −3.6 (4) | N1—C2—C3—C4 | −0.6 (10) |
O5—Sn1—N1—C6 | 5.5 (6) | C1—C2—C3—C4 | 176.0 (6) |
O1—Sn1—N1—C6 | 178.8 (5) | C2—C3—C4—C5 | −0.4 (11) |
C9—Sn1—O1—C1 | −109.6 (5) | C3—C4—C5—C6 | 0.4 (10) |
C8—Sn1—O1—C1 | 81.9 (5) | C2—N1—C6—C5 | −1.6 (9) |
O3—Sn1—O1—C1 | −13.4 (6) | Sn1—N1—C6—C5 | −174.5 (5) |
N1—Sn1—O1—C1 | −10.1 (4) | C2—N1—C6—C7 | 177.2 (5) |
O5—Sn1—O1—C1 | 163.3 (4) | Sn1—N1—C6—C7 | 4.3 (7) |
C9—Sn1—O3—C7 | 98.4 (6) | C4—C5—C6—N1 | 0.6 (10) |
C8—Sn1—O3—C7 | −86.3 (6) | C4—C5—C6—C7 | −178.1 (7) |
N1—Sn1—O3—C7 | 2.3 (5) | Sn1—O3—C7—O4 | 177.9 (6) |
O5—Sn1—O3—C7 | −172.6 (6) | Sn1—O3—C7—C6 | −0.8 (9) |
O1—Sn1—O3—C7 | 5.5 (7) | N1—C6—C7—O4 | 178.8 (7) |
Sn1—O1—C1—O2 | −166.9 (6) | C5—C6—C7—O4 | −2.4 (11) |
Sn1—O1—C1—C2 | 12.2 (7) | N1—C6—C7—O3 | −2.4 (9) |
C6—N1—C2—C3 | 1.7 (9) | C5—C6—C7—O3 | 176.4 (7) |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn2(CH3)4(C7H3NO4)2(H2O)2] |
Mr | 663.76 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 11.319 (5), 10.705 (4), 18.768 (8) |
β (°) | 91.864 (5) |
V (Å3) | 2272.9 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.25 |
Crystal size (mm) | 0.23 × 0.17 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.625, 0.743 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5571, 1998, 1645 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.123, 1.00 |
No. of reflections | 1998 |
No. of parameters | 147 |
No. of restraints | 4 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.99, −1.94 |
Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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In recent years, organotin complexes have been attracting more and more attention due to their wide industrial applications and biological activities (Dubey & Roy, 2003). Organotin(IV) dicarboxylates have been studied in considerable detail, and in general the reported organotin dicarboxylates exist as dinuclear, one-dimensional zigzag chain and cyclic structures (Ma et al., 2005). Herein we report the structure of the title complex (Fig. 1). For the coordination of the SnIV atom, two C atoms of the methyl groups are in the apical positions[C—Sn—C = 167.1 (3)°], and four O atoms and one N atom are in the equatorial positions giving a slightly distorted pentagonal- bipyramidal environment. The Sn—O, Sn—N bond distances are comparable to those reported in the literature (Aizawa et al., 1996). The longest Sn—O distance is 2.634 (5)Å for Sn—Oi [symmetry code: (i) 1 - x, -y, 1 - z].