Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041449/jh6029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041449/jh6029Isup2.hkl |
CCDC reference: 296594
[(CH3)3SiCH2]2SnCl2 (1.46 g), p-N2O1C6H4COOH (1.33 g) and triethylamine (0.81 g) were mixed in 40 ml toluene and heated for several hours under reflux. The solvent was removed and the residue recrystallized from toluene. Single crystals suitable for X-ray diffraction analysis precipitated after several days (m.p. 411.5 K).
H atoms were placed at calculated positions (C—H = 0.93–0.97 Å)
and refined as riding, with Uiso(H) = 1.2 or 1.5 time Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; molecular graphics: APEX2; software used to prepare material for publication: APEX2.
Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at 30% probability level. |
[Sn(C7H4N2O3)2(C4H11Si)2] | F(000) = 1272 |
Mr = 625.35 | Dx = 1.442 Mg m−3 |
Monoclinic, P21/n | Melting point: 411.5 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2840 (6) Å | Cell parameters from 5648 reflections |
b = 13.2343 (7) Å | θ = 2.3–25.2° |
c = 18.0000 (9) Å | µ = 1.01 mm−1 |
β = 100.056 (1)° | T = 296 K |
V = 2881.3 (3) Å3 | Block, colourless |
Z = 4 | 0.46 × 0.40 × 0.30 mm |
Bruker APEXII CCD area-detector diffractometer | 5138 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 27.0°, θmin = 1.9° |
ϕ and ω scans | h = −15→15 |
19783 measured reflections | k = −16→16 |
6218 independent reflections | l = −22→21 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0389P)2 + 0.3107P] where P = (Fo2 + 2Fc2)/3 |
6218 reflections | (Δ/σ)max = 0.001 |
322 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
[Sn(C7H4N2O3)2(C4H11Si)2] | V = 2881.3 (3) Å3 |
Mr = 625.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.2840 (6) Å | µ = 1.01 mm−1 |
b = 13.2343 (7) Å | T = 296 K |
c = 18.0000 (9) Å | 0.46 × 0.40 × 0.30 mm |
β = 100.056 (1)° |
Bruker APEXII CCD area-detector diffractometer | 5138 reflections with I > 2σ(I) |
19783 measured reflections | Rint = 0.021 |
6218 independent reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.34 e Å−3 |
6218 reflections | Δρmin = −0.41 e Å−3 |
322 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 | ||
C1 | 0.26503 (16) | 0.10102 (16) | 0.09951 (11) | 0.0572 (5) | |
C2 | 0.30843 (15) | 0.03523 (14) | 0.04388 (11) | 0.0526 (4) | |
C3 | 0.36326 (17) | −0.05319 (16) | 0.06699 (12) | 0.0606 (5) | |
H3 | 0.3705 | −0.0732 | 0.1171 | 0.073* | |
C4 | 0.40726 (18) | −0.11200 (15) | 0.01708 (12) | 0.0624 (5) | |
H4 | 0.4455 | −0.1710 | 0.0330 | 0.075* | |
C5 | 0.39365 (17) | −0.08189 (16) | −0.05691 (12) | 0.0598 (5) | |
C6 | 0.3376 (2) | 0.00529 (17) | −0.08206 (12) | 0.0691 (6) | |
H6 | 0.3288 | 0.0240 | −0.1326 | 0.083* | |
C7 | 0.29515 (18) | 0.06399 (17) | −0.03104 (12) | 0.0638 (5) | |
H7 | 0.2574 | 0.1232 | −0.0469 | 0.077* | |
C8 | 0.18736 (18) | 0.10789 (16) | 0.36655 (11) | 0.0592 (5) | |
C9 | 0.17765 (16) | 0.04718 (14) | 0.43457 (10) | 0.0528 (4) | |
C10 | 0.1389 (2) | 0.09138 (16) | 0.49456 (12) | 0.0663 (5) | |
H10 | 0.1200 | 0.1595 | 0.4925 | 0.080* | |
C11 | 0.1279 (2) | 0.03555 (16) | 0.55708 (12) | 0.0689 (6) | |
H11 | 0.1024 | 0.0651 | 0.5977 | 0.083* | |
C12 | 0.15568 (18) | −0.06508 (16) | 0.55821 (11) | 0.0612 (5) | |
C13 | 0.1938 (2) | −0.11113 (16) | 0.49983 (12) | 0.0680 (6) | |
H13 | 0.2119 | −0.1794 | 0.5020 | 0.082* | |
C14 | 0.20467 (19) | −0.05406 (15) | 0.43773 (11) | 0.0630 (5) | |
H14 | 0.2305 | −0.0840 | 0.3974 | 0.076* | |
C15 | 0.3292 (2) | 0.28824 (18) | 0.24683 (14) | 0.0734 (6) | |
H15A | 0.3588 | 0.2930 | 0.2004 | 0.088* | |
H15B | 0.2915 | 0.3516 | 0.2520 | 0.088* | |
C16 | 0.03599 (18) | 0.17051 (14) | 0.18590 (13) | 0.0597 (5) | |
H16A | 0.0265 | 0.1308 | 0.1400 | 0.072* | |
H16B | 0.0014 | 0.1331 | 0.2219 | 0.072* | |
C17 | 0.5633 (3) | 0.3536 (3) | 0.28876 (19) | 0.1027 (9) | |
H17A | 0.5394 | 0.4212 | 0.2751 | 0.154* | |
H17B | 0.5799 | 0.3191 | 0.2452 | 0.154* | |
H17C | 0.6282 | 0.3559 | 0.3271 | 0.154* | |
C18 | 0.4959 (2) | 0.15340 (19) | 0.35098 (16) | 0.0858 (7) | |
H18A | 0.5641 | 0.1547 | 0.3864 | 0.129* | |
H18B | 0.5067 | 0.1176 | 0.3064 | 0.129* | |
H18C | 0.4402 | 0.1200 | 0.3733 | 0.129* | |
C19 | 0.4188 (3) | 0.3509 (3) | 0.40974 (17) | 0.1056 (10) | |
H19A | 0.4850 | 0.3579 | 0.4466 | 0.158* | |
H19B | 0.3653 | 0.3124 | 0.4308 | 0.158* | |
H19C | 0.3891 | 0.4166 | 0.3955 | 0.158* | |
C20 | −0.0058 (3) | 0.3548 (2) | 0.08153 (17) | 0.1019 (9) | |
H20A | −0.0559 | 0.4098 | 0.0669 | 0.153* | |
H20B | −0.0098 | 0.3080 | 0.0403 | 0.153* | |
H20C | 0.0682 | 0.3804 | 0.0945 | 0.153* | |
C21 | −0.1914 (2) | 0.2512 (3) | 0.1446 (2) | 0.1302 (14) | |
H21A | −0.2069 | 0.2091 | 0.1849 | 0.195* | |
H21B | −0.2062 | 0.2143 | 0.0979 | 0.195* | |
H21C | −0.2374 | 0.3103 | 0.1409 | 0.195* | |
C22 | −0.0182 (3) | 0.3740 (2) | 0.24675 (16) | 0.1059 (10) | |
H22A | 0.0540 | 0.4035 | 0.2508 | 0.159* | |
H22B | −0.0223 | 0.3359 | 0.2915 | 0.159* | |
H22C | −0.0728 | 0.4266 | 0.2410 | 0.159* | |
N1 | 0.44255 (18) | −0.14431 (17) | −0.11067 (13) | 0.0776 (6) | |
N2 | 0.1423 (2) | −0.12599 (19) | 0.62458 (12) | 0.0885 (6) | |
O1 | 0.27447 (12) | 0.06662 (11) | 0.16745 (8) | 0.0639 (4) | |
O2 | 0.22324 (14) | 0.18443 (11) | 0.08214 (9) | 0.0690 (4) | |
O3 | 0.22469 (12) | 0.06401 (11) | 0.31257 (8) | 0.0637 (4) | |
O4 | 0.15964 (16) | 0.19826 (11) | 0.36071 (9) | 0.0761 (4) | |
O5 | 0.4342 (2) | −0.11352 (17) | −0.17446 (13) | 0.1234 (9) | |
O6 | 0.48740 (17) | −0.22306 (16) | −0.08807 (13) | 0.0985 (6) | |
O7 | 0.1141 (3) | −0.08365 (19) | 0.67708 (12) | 0.1409 (10) | |
O8 | 0.1587 (3) | −0.21558 (18) | 0.62328 (14) | 0.1352 (10) | |
Si1 | 0.45119 (5) | 0.28490 (5) | 0.32541 (3) | 0.06287 (15) | |
Si2 | −0.04408 (5) | 0.28958 (5) | 0.16391 (3) | 0.05789 (14) | |
Sn1 | 0.206338 (11) | 0.176298 (10) | 0.228867 (7) | 0.05313 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0556 (11) | 0.0642 (12) | 0.0547 (11) | −0.0021 (9) | 0.0178 (9) | 0.0024 (9) |
C2 | 0.0515 (10) | 0.0571 (11) | 0.0512 (10) | −0.0051 (8) | 0.0148 (8) | 0.0023 (8) |
C3 | 0.0689 (13) | 0.0620 (12) | 0.0520 (11) | −0.0011 (9) | 0.0135 (9) | 0.0060 (9) |
C4 | 0.0681 (13) | 0.0513 (11) | 0.0696 (13) | −0.0020 (9) | 0.0170 (10) | −0.0015 (9) |
C5 | 0.0607 (12) | 0.0576 (12) | 0.0664 (13) | −0.0175 (9) | 0.0257 (10) | −0.0108 (10) |
C6 | 0.0880 (16) | 0.0715 (14) | 0.0513 (12) | −0.0090 (11) | 0.0222 (10) | 0.0027 (10) |
C7 | 0.0748 (14) | 0.0639 (12) | 0.0551 (11) | 0.0047 (10) | 0.0181 (10) | 0.0087 (10) |
C8 | 0.0702 (13) | 0.0580 (12) | 0.0502 (11) | −0.0035 (9) | 0.0125 (9) | 0.0019 (9) |
C9 | 0.0610 (11) | 0.0518 (10) | 0.0466 (10) | −0.0029 (8) | 0.0119 (8) | −0.0011 (8) |
C10 | 0.0949 (16) | 0.0506 (11) | 0.0571 (12) | 0.0044 (10) | 0.0233 (11) | −0.0054 (9) |
C11 | 0.0953 (16) | 0.0620 (13) | 0.0550 (12) | −0.0015 (11) | 0.0288 (11) | −0.0080 (10) |
C12 | 0.0756 (13) | 0.0608 (12) | 0.0497 (11) | −0.0034 (10) | 0.0178 (10) | 0.0051 (9) |
C13 | 0.0981 (17) | 0.0492 (11) | 0.0615 (13) | 0.0111 (10) | 0.0275 (11) | 0.0038 (9) |
C14 | 0.0856 (15) | 0.0564 (12) | 0.0519 (11) | 0.0085 (10) | 0.0260 (10) | −0.0031 (9) |
C15 | 0.0763 (14) | 0.0681 (13) | 0.0713 (14) | −0.0098 (11) | 0.0008 (11) | 0.0165 (11) |
C16 | 0.0613 (12) | 0.0575 (12) | 0.0635 (13) | −0.0079 (9) | 0.0195 (10) | −0.0049 (9) |
C17 | 0.088 (2) | 0.107 (2) | 0.111 (2) | −0.0234 (17) | 0.0126 (17) | 0.0005 (19) |
C18 | 0.0947 (19) | 0.0809 (16) | 0.0799 (17) | 0.0202 (14) | 0.0096 (14) | 0.0066 (13) |
C19 | 0.131 (3) | 0.105 (2) | 0.0815 (19) | 0.0280 (19) | 0.0199 (18) | −0.0185 (16) |
C20 | 0.139 (3) | 0.0895 (18) | 0.0834 (19) | −0.0022 (18) | 0.0375 (18) | 0.0162 (16) |
C21 | 0.0600 (16) | 0.142 (3) | 0.178 (4) | −0.0072 (17) | −0.0096 (19) | 0.045 (3) |
C22 | 0.160 (3) | 0.0770 (18) | 0.0803 (18) | 0.0182 (18) | 0.0185 (18) | −0.0164 (14) |
N1 | 0.0828 (14) | 0.0724 (13) | 0.0868 (16) | −0.0251 (11) | 0.0406 (11) | −0.0211 (11) |
N2 | 0.1257 (19) | 0.0824 (15) | 0.0662 (13) | −0.0023 (13) | 0.0410 (12) | 0.0115 (11) |
O1 | 0.0748 (9) | 0.0697 (9) | 0.0513 (8) | 0.0092 (7) | 0.0221 (7) | 0.0039 (7) |
O2 | 0.0769 (10) | 0.0668 (10) | 0.0680 (10) | 0.0119 (7) | 0.0262 (8) | 0.0071 (7) |
O3 | 0.0799 (9) | 0.0638 (9) | 0.0514 (8) | 0.0051 (7) | 0.0229 (7) | 0.0073 (6) |
O4 | 0.1101 (13) | 0.0548 (9) | 0.0658 (10) | 0.0050 (8) | 0.0219 (9) | 0.0065 (7) |
O5 | 0.203 (3) | 0.0965 (15) | 0.0944 (15) | −0.0139 (14) | 0.0904 (16) | −0.0144 (12) |
O6 | 0.0978 (14) | 0.0856 (13) | 0.1184 (16) | 0.0087 (11) | 0.0367 (12) | −0.0271 (12) |
O7 | 0.248 (3) | 0.1110 (17) | 0.0868 (14) | 0.0103 (19) | 0.0943 (18) | 0.0160 (13) |
O8 | 0.238 (3) | 0.0766 (14) | 0.1082 (17) | 0.0210 (17) | 0.0791 (18) | 0.0340 (13) |
Si1 | 0.0658 (4) | 0.0642 (3) | 0.0577 (3) | 0.0029 (3) | 0.0082 (3) | −0.0029 (3) |
Si2 | 0.0556 (3) | 0.0636 (3) | 0.0533 (3) | −0.0028 (2) | 0.0065 (2) | −0.0012 (3) |
Sn1 | 0.05880 (10) | 0.05379 (9) | 0.04876 (9) | 0.00165 (5) | 0.01477 (6) | 0.00473 (5) |
C1—O2 | 1.234 (2) | C16—H16A | 0.9700 |
C1—O1 | 1.291 (2) | C16—H16B | 0.9700 |
C1—C2 | 1.494 (3) | C17—Si1 | 1.864 (3) |
C2—C3 | 1.378 (3) | C17—H17A | 0.9600 |
C2—C7 | 1.383 (3) | C17—H17B | 0.9600 |
C3—C4 | 1.369 (3) | C17—H17C | 0.9600 |
C3—H3 | 0.9300 | C18—Si1 | 1.859 (2) |
C4—C5 | 1.372 (3) | C18—H18A | 0.9600 |
C4—H4 | 0.9300 | C18—H18B | 0.9600 |
C5—C6 | 1.379 (3) | C18—H18C | 0.9600 |
C5—N1 | 1.477 (3) | C19—Si1 | 1.854 (3) |
C6—C7 | 1.374 (3) | C19—H19A | 0.9600 |
C6—H6 | 0.9300 | C19—H19B | 0.9600 |
C7—H7 | 0.9300 | C19—H19C | 0.9600 |
C8—O4 | 1.243 (2) | C20—Si2 | 1.846 (3) |
C8—O3 | 1.284 (2) | C20—H20A | 0.9600 |
C8—C9 | 1.486 (3) | C20—H20B | 0.9600 |
C9—C14 | 1.379 (3) | C20—H20C | 0.9600 |
C9—C10 | 1.384 (3) | C21—Si2 | 1.853 (3) |
C10—C11 | 1.372 (3) | C21—H21A | 0.9600 |
C10—H10 | 0.9300 | C21—H21B | 0.9600 |
C11—C12 | 1.374 (3) | C21—H21C | 0.9600 |
C11—H11 | 0.9300 | C22—Si2 | 1.846 (3) |
C12—C13 | 1.366 (3) | C22—H22A | 0.9600 |
C12—N2 | 1.474 (3) | C22—H22B | 0.9600 |
C13—C14 | 1.375 (3) | C22—H22C | 0.9600 |
C13—H13 | 0.9300 | N1—O5 | 1.206 (3) |
C14—H14 | 0.9300 | N1—O6 | 1.215 (3) |
C15—Si1 | 1.873 (2) | N2—O7 | 1.201 (3) |
C15—Sn1 | 2.099 (2) | N2—O8 | 1.203 (3) |
C15—H15A | 0.9700 | O1—Sn1 | 2.0862 (14) |
C15—H15B | 0.9700 | O2—Sn1 | 2.6874 (16) |
C16—Si2 | 1.863 (2) | O3—Sn1 | 2.1001 (13) |
C16—Sn1 | 2.102 (2) | O4—Sn1 | 2.5537 (17) |
O2—C1—O1 | 121.33 (19) | H18A—C18—H18C | 109.5 |
O2—C1—C2 | 122.18 (18) | H18B—C18—H18C | 109.5 |
O1—C1—C2 | 116.49 (18) | Si1—C19—H19A | 109.5 |
C3—C2—C7 | 119.76 (19) | Si1—C19—H19B | 109.5 |
C3—C2—C1 | 120.36 (18) | H19A—C19—H19B | 109.5 |
C7—C2—C1 | 119.87 (18) | Si1—C19—H19C | 109.5 |
C4—C3—C2 | 120.85 (19) | H19A—C19—H19C | 109.5 |
C4—C3—H3 | 119.6 | H19B—C19—H19C | 109.5 |
C2—C3—H3 | 119.6 | Si2—C20—H20A | 109.5 |
C3—C4—C5 | 118.5 (2) | Si2—C20—H20B | 109.5 |
C3—C4—H4 | 120.8 | H20A—C20—H20B | 109.5 |
C5—C4—H4 | 120.8 | Si2—C20—H20C | 109.5 |
C4—C5—C6 | 122.1 (2) | H20A—C20—H20C | 109.5 |
C4—C5—N1 | 118.6 (2) | H20B—C20—H20C | 109.5 |
C6—C5—N1 | 119.3 (2) | Si2—C21—H21A | 109.5 |
C7—C6—C5 | 118.7 (2) | Si2—C21—H21B | 109.5 |
C7—C6—H6 | 120.7 | H21A—C21—H21B | 109.5 |
C5—C6—H6 | 120.7 | Si2—C21—H21C | 109.5 |
C6—C7—C2 | 120.1 (2) | H21A—C21—H21C | 109.5 |
C6—C7—H7 | 119.9 | H21B—C21—H21C | 109.5 |
C2—C7—H7 | 119.9 | Si2—C22—H22A | 109.5 |
O4—C8—O3 | 120.01 (18) | Si2—C22—H22B | 109.5 |
O4—C8—C9 | 121.98 (19) | H22A—C22—H22B | 109.5 |
O3—C8—C9 | 118.01 (18) | Si2—C22—H22C | 109.5 |
C14—C9—C10 | 119.44 (18) | H22A—C22—H22C | 109.5 |
C14—C9—C8 | 120.38 (18) | H22B—C22—H22C | 109.5 |
C10—C9—C8 | 120.16 (18) | O5—N1—O6 | 124.5 (2) |
C11—C10—C9 | 120.6 (2) | O5—N1—C5 | 117.3 (2) |
C11—C10—H10 | 119.7 | O6—N1—C5 | 118.2 (2) |
C9—C10—H10 | 119.7 | O7—N2—O8 | 123.2 (2) |
C12—C11—C10 | 118.3 (2) | O7—N2—C12 | 118.1 (2) |
C12—C11—H11 | 120.8 | O8—N2—C12 | 118.7 (2) |
C10—C11—H11 | 120.8 | C1—O1—Sn1 | 106.18 (13) |
C13—C12—C11 | 122.58 (19) | C1—O2—Sn1 | 79.35 (12) |
C13—C12—N2 | 118.7 (2) | C8—O3—Sn1 | 102.42 (12) |
C11—C12—N2 | 118.7 (2) | C8—O4—Sn1 | 82.32 (12) |
C12—C13—C14 | 118.38 (19) | C19—Si1—C18 | 109.57 (14) |
C12—C13—H13 | 120.8 | C19—Si1—C17 | 109.73 (16) |
C14—C13—H13 | 120.8 | C18—Si1—C17 | 109.85 (15) |
C13—C14—C9 | 120.69 (19) | C19—Si1—C15 | 110.44 (14) |
C13—C14—H14 | 119.7 | C18—Si1—C15 | 111.85 (12) |
C9—C14—H14 | 119.7 | C17—Si1—C15 | 105.31 (13) |
Si1—C15—Sn1 | 123.96 (12) | C22—Si2—C20 | 109.50 (15) |
Si1—C15—H15A | 106.3 | C22—Si2—C21 | 110.03 (18) |
Sn1—C15—H15A | 106.3 | C20—Si2—C21 | 110.77 (17) |
Si1—C15—H15B | 106.3 | C22—Si2—C16 | 109.29 (12) |
Sn1—C15—H15B | 106.3 | C20—Si2—C16 | 111.52 (13) |
H15A—C15—H15B | 106.4 | C21—Si2—C16 | 105.66 (14) |
Si2—C16—Sn1 | 120.14 (10) | O1—Sn1—C15 | 103.20 (9) |
Si2—C16—H16A | 107.3 | O1—Sn1—O3 | 83.40 (5) |
Sn1—C16—H16A | 107.3 | C15—Sn1—O3 | 113.87 (7) |
Si2—C16—H16B | 107.3 | O1—Sn1—C16 | 104.21 (7) |
Sn1—C16—H16B | 107.3 | C15—Sn1—C16 | 136.49 (8) |
H16A—C16—H16B | 106.9 | O3—Sn1—C16 | 102.32 (7) |
Si1—C17—H17A | 109.5 | O1—Sn1—O4 | 138.39 (5) |
Si1—C17—H17B | 109.5 | C15—Sn1—O4 | 92.79 (9) |
H17A—C17—H17B | 109.5 | O3—Sn1—O4 | 55.06 (5) |
Si1—C17—H17C | 109.5 | C16—Sn1—O4 | 88.59 (7) |
H17A—C17—H17C | 109.5 | O1—Sn1—O2 | 53.14 (5) |
H17B—C17—H17C | 109.5 | C15—Sn1—O2 | 86.92 (8) |
Si1—C18—H18A | 109.5 | O3—Sn1—O2 | 135.75 (5) |
Si1—C18—H18B | 109.5 | C16—Sn1—O2 | 83.26 (7) |
H18A—C18—H18B | 109.5 | O4—Sn1—O2 | 167.76 (5) |
Si1—C18—H18C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Sn(C7H4N2O3)2(C4H11Si)2] |
Mr | 625.35 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 12.2840 (6), 13.2343 (7), 18.0000 (9) |
β (°) | 100.056 (1) |
V (Å3) | 2881.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.01 |
Crystal size (mm) | 0.46 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19783, 6218, 5138 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.069, 1.02 |
No. of reflections | 6218 |
No. of parameters | 322 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.41 |
Computer programs: APEX2 (Bruker, 2004), APEX2.
C15—Sn1 | 2.099 (2) | O2—Sn1 | 2.6874 (16) |
C16—Sn1 | 2.102 (2) | O3—Sn1 | 2.1001 (13) |
O1—Sn1 | 2.0862 (14) | O4—Sn1 | 2.5537 (17) |
Si1—C15—Sn1 | 123.96 (12) | O3—Sn1—C16 | 102.32 (7) |
Si2—C16—Sn1 | 120.14 (10) | O1—Sn1—O4 | 138.39 (5) |
C1—O1—Sn1 | 106.18 (13) | C15—Sn1—O4 | 92.79 (9) |
C1—O2—Sn1 | 79.35 (12) | O3—Sn1—O4 | 55.06 (5) |
C8—O3—Sn1 | 102.42 (12) | C16—Sn1—O4 | 88.59 (7) |
C8—O4—Sn1 | 82.32 (12) | O1—Sn1—O2 | 53.14 (5) |
O1—Sn1—C15 | 103.20 (9) | C15—Sn1—O2 | 86.92 (8) |
O1—Sn1—O3 | 83.40 (5) | O3—Sn1—O2 | 135.75 (5) |
C15—Sn1—O3 | 113.87 (7) | C16—Sn1—O2 | 83.26 (7) |
O1—Sn1—C16 | 104.21 (7) | O4—Sn1—O2 | 167.76 (5) |
C15—Sn1—C16 | 136.49 (8) |
Many methods have been developed to decrease the toxicity of organotin compounds, and organosilicon ligands have been shown to be effective (Xie & Liu, 1998). Research has shown that the biological activity of diorganotin compounds depends mainly n the alkyl groups and the ligands (Gielen, 1996; Yang et al., 1996). The structure of the title compound, (I), is analogous to bis(4-methoxylbenzoato)phenyl(trimethylsilylmethyl)tin(IV) which we have reported previously (Lin et al., 2005).
The carboxylate groups act as asymmetric chelating groups. In each carboxylate group, one Sn—O bond is much longer then the other. The carboxylate O atoms coordinate strongly to the Sn atom [Sn—O = 2.0862 (14) and 2.1001 (13) Å] while the carbonyl O atoms are much more weakly bound [Sn—O = 2.6874 (16) and 2.5537 (17) Å]. All Sn—O distances are within expected ranges.
The angle between the two strongly bound cis- O atoms, O1—Sn1—O3, is 83.40 (5)°, while for the weakly bound O atoms O4—Sn1—O2 is 167.75 (5)°, leaving one side of the Sn atom open to bind the two axial ligands [C15—Sn1—C16 = 136.49 (8)°]. There are no classical hydrogen bonds in the crystal structure.