Acta Cryst. (2009). E65, m1441 [ doi:10.1107/S1600536809043591 ]
In the title compound, [Sn(C6H5)2(C18H12N2O3)], the SnIV atom has a distorted trigonal-bipyramidal geometry. The Schiff base molecule is coordinated to the SnIV atom in a tridentate fashion via the azomethine N atom, the hydroxy O atom and the carbonyl O atom. The complex involves an intramolecular O-H
N hydrogen bond.
2-Hydroxybenzhydrazide (5 mol) was added to 30 ml ethanol. The mixture was stirred for 0.5 h and then 2-hyroxy-1-naphthyldehyde (5 mol) was added, generating a yellow sediment immediately. The product was recrystallized from ethanol and DMF mixed solvent to get yellow crystals of 2-hydroxy-1-naphthaldehyde 2-benzoylhydrazone (L). The preparation of the title compound was carried out under nitrogen atmosphere. L (4 mmol) was added to a mixture of ethanol and benzene (v/v 1:3, 30 ml) with sodium ethoxide (4 mmol). The mixture was stirred for 0.5 h and then dichlorodiphenyltin (4 mmol) was added. The mixture was stirred for 12 h under reflux. After cooling to room temperature, the mixture was filtered and evaporated to dryness. The resulting solid was then recrystallized from dichloromethane-hexane (v/v 1:1). Analysis, calculated for C30H22N2O3Sn: C 62.42, H 3.84, N 4.85, O 8.32%; found: C 62.30, H 3.75, N 4.92, O 8.28%.
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and O—H = 0.82 Å and with Uiso(H) = 1.2(1.5 for hydroxyl)Ueq(C, O).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
| Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. |
| Fig. 2. The crystal packing of the title compound. |
| [Sn(C6H5)2(C18H12N2O3)] | F(000) = 1160 |
| Mr = 577.19 | Dx = 1.518 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 4435 reflections |
| a = 9.418 (1) Å | θ = 2.5–24.5° |
| b = 11.0861 (12) Å | µ = 1.05 mm−1 |
| c = 25.668 (2) Å | T = 293 K |
| β = 109.547 (2)° | Block, colorless |
| V = 2525.5 (4) Å3 | 0.43 × 0.29 × 0.20 mm |
| Z = 4 |
| Siemens SMART 1000 CCD diffractometer | 4435 independent reflections |
| Radiation source: fine-focus sealed tube | 3263 reflections with I > 2σ(I) |
| graphite | Rint = 0.031 |
| φ and ω scans | θmax = 25.0°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.662, Tmax = 0.818 | k = −11→13 |
| 12414 measured reflections | l = −30→30 |
| 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.073 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0238P)2 + 1.7663P] where P = (Fo2 + 2Fc2)/3 |
| 4435 reflections | (Δ/σ)max = 0.003 |
| 325 parameters | Δρmax = 0.43 e Å−3 |
| 0 restraints | Δρmin = −0.33 e Å−3 |
| [Sn(C6H5)2(C18H12N2O3)] | V = 2525.5 (4) Å3 |
| Mr = 577.19 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.418 (1) Å | µ = 1.05 mm−1 |
| b = 11.0861 (12) Å | T = 293 K |
| c = 25.668 (2) Å | 0.43 × 0.29 × 0.20 mm |
| β = 109.547 (2)° |
| Siemens SMART 1000 CCD diffractometer | 4435 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3263 reflections with I > 2σ(I) |
| Tmin = 0.662, Tmax = 0.818 | Rint = 0.031 |
| 12414 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
| wR(F2) = 0.073 | Δρmax = 0.43 e Å−3 |
| S = 1.03 | Δρmin = −0.33 e Å−3 |
| 4435 reflections | Absolute structure: ? |
| 325 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.89811 (3) | 0.74107 (2) | 0.920886 (10) | 0.04851 (10) | |
| N1 | 0.8396 (4) | 0.4718 (2) | 0.91811 (11) | 0.0465 (8) | |
| N2 | 0.8343 (3) | 0.5736 (2) | 0.94938 (11) | 0.0434 (7) | |
| O1 | 0.9135 (3) | 0.6067 (2) | 0.86422 (10) | 0.0647 (8) | |
| O2 | 0.7809 (4) | 0.2520 (2) | 0.88057 (12) | 0.0834 (10) | |
| H2 | 0.7848 | 0.3089 | 0.9015 | 0.125* | |
| O3 | 0.8815 (3) | 0.8048 (2) | 0.99407 (10) | 0.0589 (7) | |
| C1 | 0.8817 (4) | 0.4984 (3) | 0.87560 (14) | 0.0459 (9) | |
| C2 | 0.8935 (4) | 0.4009 (3) | 0.83892 (14) | 0.0493 (9) | |
| C3 | 0.8422 (5) | 0.2849 (3) | 0.84222 (15) | 0.0576 (11) | |
| C4 | 0.8529 (6) | 0.1978 (4) | 0.80504 (18) | 0.0794 (14) | |
| H4 | 0.8193 | 0.1198 | 0.8075 | 0.095* | |
| C5 | 0.9126 (7) | 0.2261 (5) | 0.7647 (2) | 0.0918 (17) | |
| H5 | 0.9166 | 0.1676 | 0.7392 | 0.110* | |
| C6 | 0.9665 (7) | 0.3391 (5) | 0.7614 (2) | 0.1001 (19) | |
| H6 | 1.0100 | 0.3573 | 0.7347 | 0.120* | |
| C7 | 0.9554 (6) | 0.4251 (4) | 0.79798 (17) | 0.0753 (14) | |
| H7 | 0.9905 | 0.5025 | 0.7954 | 0.090* | |
| C8 | 0.7840 (4) | 0.5562 (3) | 0.99031 (14) | 0.0449 (9) | |
| H8 | 0.7550 | 0.4779 | 0.9950 | 0.054* | |
| C9 | 0.7683 (4) | 0.6439 (3) | 1.02883 (13) | 0.0428 (9) | |
| C10 | 0.8202 (4) | 0.7625 (3) | 1.02946 (14) | 0.0482 (9) | |
| C11 | 0.8110 (5) | 0.8440 (3) | 1.07056 (15) | 0.0557 (10) | |
| H11 | 0.8460 | 0.9225 | 1.0708 | 0.067* | |
| C12 | 0.7523 (5) | 0.8097 (4) | 1.10938 (16) | 0.0609 (11) | |
| H12 | 0.7496 | 0.8648 | 1.1364 | 0.073* | |
| C13 | 0.6946 (5) | 0.6924 (4) | 1.11023 (16) | 0.0561 (11) | |
| C14 | 0.7010 (4) | 0.6071 (3) | 1.07003 (15) | 0.0507 (10) | |
| C15 | 0.6398 (5) | 0.4933 (4) | 1.07211 (17) | 0.0640 (12) | |
| H15 | 0.6401 | 0.4363 | 1.0455 | 0.077* | |
| C16 | 0.5797 (6) | 0.4627 (4) | 1.1119 (2) | 0.0826 (15) | |
| H16 | 0.5410 | 0.3856 | 1.1122 | 0.099* | |
| C17 | 0.5756 (6) | 0.5453 (5) | 1.1519 (2) | 0.0878 (16) | |
| H17 | 0.5346 | 0.5242 | 1.1790 | 0.105* | |
| C18 | 0.6327 (6) | 0.6582 (4) | 1.15106 (18) | 0.0751 (14) | |
| H18 | 0.6308 | 0.7137 | 1.1780 | 0.090* | |
| C19 | 1.1244 (4) | 0.7942 (3) | 0.93967 (14) | 0.0444 (9) | |
| C20 | 1.2167 (5) | 0.8207 (3) | 0.99286 (15) | 0.0572 (11) | |
| H20 | 1.1779 | 0.8179 | 1.0217 | 0.069* | |
| C21 | 1.3657 (5) | 0.8514 (4) | 1.0035 (2) | 0.0748 (13) | |
| H21 | 1.4275 | 0.8661 | 1.0396 | 0.090* | |
| C22 | 1.4234 (6) | 0.8602 (4) | 0.9612 (2) | 0.0763 (13) | |
| H22 | 1.5236 | 0.8821 | 0.9686 | 0.092* | |
| C23 | 1.3339 (6) | 0.8371 (4) | 0.9084 (2) | 0.0707 (13) | |
| H23 | 1.3723 | 0.8445 | 0.8796 | 0.085* | |
| C24 | 1.1862 (5) | 0.8026 (3) | 0.89768 (16) | 0.0585 (11) | |
| H24 | 1.1268 | 0.7846 | 0.8616 | 0.070* | |
| C25 | 0.7141 (4) | 0.8331 (3) | 0.86445 (15) | 0.0508 (10) | |
| C26 | 0.6817 (5) | 0.9491 (4) | 0.87485 (19) | 0.0700 (12) | |
| H26 | 0.7412 | 0.9868 | 0.9071 | 0.084* | |
| C27 | 0.5624 (6) | 1.0113 (5) | 0.8384 (2) | 0.0913 (16) | |
| H27 | 0.5436 | 1.0907 | 0.8459 | 0.110* | |
| C28 | 0.4723 (6) | 0.9565 (7) | 0.7916 (2) | 0.0969 (19) | |
| H28 | 0.3911 | 0.9980 | 0.7674 | 0.116* | |
| C29 | 0.5006 (6) | 0.8424 (7) | 0.7803 (2) | 0.0976 (18) | |
| H29 | 0.4386 | 0.8050 | 0.7484 | 0.117* | |
| C30 | 0.6228 (5) | 0.7797 (4) | 0.81640 (18) | 0.0751 (13) | |
| H30 | 0.6427 | 0.7013 | 0.8079 | 0.090* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.05637 (18) | 0.04439 (15) | 0.04495 (15) | −0.01070 (14) | 0.01717 (12) | −0.00358 (12) |
| N1 | 0.058 (2) | 0.0411 (16) | 0.0412 (17) | −0.0028 (14) | 0.0175 (16) | −0.0055 (13) |
| N2 | 0.048 (2) | 0.0421 (16) | 0.0400 (17) | −0.0043 (14) | 0.0142 (15) | −0.0034 (13) |
| O1 | 0.094 (2) | 0.0545 (16) | 0.0572 (17) | −0.0219 (15) | 0.0407 (17) | −0.0132 (13) |
| O2 | 0.138 (3) | 0.0483 (16) | 0.079 (2) | −0.0149 (18) | 0.057 (2) | −0.0112 (15) |
| O3 | 0.080 (2) | 0.0532 (15) | 0.0504 (16) | −0.0166 (14) | 0.0309 (15) | −0.0128 (12) |
| C1 | 0.048 (3) | 0.046 (2) | 0.039 (2) | −0.0072 (18) | 0.0094 (18) | −0.0046 (16) |
| C2 | 0.054 (3) | 0.054 (2) | 0.036 (2) | −0.0022 (19) | 0.0113 (19) | −0.0059 (17) |
| C3 | 0.071 (3) | 0.053 (2) | 0.045 (2) | 0.008 (2) | 0.014 (2) | −0.0043 (18) |
| C4 | 0.114 (4) | 0.057 (3) | 0.067 (3) | 0.009 (3) | 0.029 (3) | −0.016 (2) |
| C5 | 0.120 (5) | 0.091 (4) | 0.065 (3) | 0.017 (3) | 0.032 (3) | −0.029 (3) |
| C6 | 0.142 (6) | 0.111 (4) | 0.064 (3) | −0.014 (4) | 0.056 (4) | −0.025 (3) |
| C7 | 0.097 (4) | 0.079 (3) | 0.057 (3) | −0.018 (3) | 0.037 (3) | −0.015 (2) |
| C8 | 0.051 (3) | 0.041 (2) | 0.044 (2) | 0.0003 (17) | 0.0162 (19) | 0.0026 (16) |
| C9 | 0.043 (2) | 0.045 (2) | 0.037 (2) | 0.0062 (17) | 0.0096 (17) | 0.0028 (15) |
| C10 | 0.047 (2) | 0.050 (2) | 0.044 (2) | 0.0035 (19) | 0.0112 (17) | −0.0021 (18) |
| C11 | 0.062 (3) | 0.050 (2) | 0.052 (2) | 0.002 (2) | 0.016 (2) | −0.0086 (18) |
| C12 | 0.068 (3) | 0.063 (3) | 0.053 (3) | 0.011 (2) | 0.021 (2) | −0.010 (2) |
| C13 | 0.060 (3) | 0.059 (2) | 0.052 (2) | 0.013 (2) | 0.023 (2) | 0.0021 (19) |
| C14 | 0.051 (3) | 0.052 (2) | 0.050 (2) | 0.0134 (19) | 0.018 (2) | 0.0057 (18) |
| C15 | 0.082 (4) | 0.058 (3) | 0.066 (3) | 0.005 (2) | 0.044 (3) | 0.003 (2) |
| C16 | 0.112 (5) | 0.071 (3) | 0.091 (4) | 0.001 (3) | 0.069 (3) | 0.007 (3) |
| C17 | 0.118 (5) | 0.089 (4) | 0.084 (4) | 0.014 (3) | 0.071 (4) | 0.014 (3) |
| C18 | 0.097 (4) | 0.077 (3) | 0.068 (3) | 0.016 (3) | 0.050 (3) | −0.003 (2) |
| C19 | 0.052 (2) | 0.0325 (18) | 0.047 (2) | −0.0046 (16) | 0.0141 (19) | 0.0030 (15) |
| C20 | 0.063 (3) | 0.062 (3) | 0.044 (2) | −0.007 (2) | 0.014 (2) | 0.0018 (18) |
| C21 | 0.059 (3) | 0.078 (3) | 0.068 (3) | −0.011 (3) | −0.004 (3) | −0.002 (2) |
| C22 | 0.055 (3) | 0.067 (3) | 0.106 (4) | −0.008 (2) | 0.027 (3) | −0.003 (3) |
| C23 | 0.076 (4) | 0.063 (3) | 0.089 (4) | −0.010 (2) | 0.048 (3) | 0.002 (2) |
| C24 | 0.067 (3) | 0.063 (2) | 0.047 (2) | −0.010 (2) | 0.022 (2) | −0.0004 (19) |
| C25 | 0.050 (3) | 0.056 (2) | 0.045 (2) | −0.0142 (19) | 0.0134 (19) | 0.0039 (17) |
| C26 | 0.059 (3) | 0.066 (3) | 0.077 (3) | −0.002 (2) | 0.012 (3) | 0.005 (2) |
| C27 | 0.080 (4) | 0.081 (4) | 0.106 (5) | 0.008 (3) | 0.021 (4) | 0.023 (3) |
| C28 | 0.058 (4) | 0.141 (6) | 0.088 (4) | 0.008 (4) | 0.019 (3) | 0.052 (4) |
| C29 | 0.070 (4) | 0.153 (6) | 0.055 (3) | −0.024 (4) | 0.001 (3) | 0.007 (4) |
| C30 | 0.076 (3) | 0.087 (3) | 0.054 (3) | −0.019 (3) | 0.011 (2) | −0.006 (2) |
| Sn1—O1 | 2.121 (2) | C13—C18 | 1.411 (5) |
| Sn1—O3 | 2.061 (2) | C13—C14 | 1.415 (5) |
| Sn1—N2 | 2.154 (3) | C14—C15 | 1.396 (5) |
| Sn1—C19 | 2.106 (4) | C15—C16 | 1.366 (5) |
| Sn1—C25 | 2.113 (4) | C15—H15 | 0.9300 |
| N1—C1 | 1.313 (4) | C16—C17 | 1.387 (6) |
| N1—N2 | 1.395 (4) | C16—H16 | 0.9300 |
| N2—C8 | 1.303 (4) | C17—C18 | 1.365 (6) |
| O1—C1 | 1.294 (4) | C17—H17 | 0.9300 |
| O2—C3 | 1.348 (5) | C18—H18 | 0.9300 |
| O2—H2 | 0.8200 | C19—C20 | 1.383 (5) |
| O3—C10 | 1.315 (4) | C19—C24 | 1.389 (5) |
| C1—C2 | 1.462 (5) | C20—C21 | 1.380 (6) |
| C2—C3 | 1.386 (5) | C20—H20 | 0.9300 |
| C2—C7 | 1.388 (5) | C21—C22 | 1.370 (6) |
| C3—C4 | 1.384 (5) | C21—H21 | 0.9300 |
| C4—C5 | 1.371 (6) | C22—C23 | 1.359 (6) |
| C4—H4 | 0.9300 | C22—H22 | 0.9300 |
| C5—C6 | 1.364 (7) | C23—C24 | 1.378 (6) |
| C5—H5 | 0.9300 | C23—H23 | 0.9300 |
| C6—C7 | 1.366 (6) | C24—H24 | 0.9300 |
| C6—H6 | 0.9300 | C25—C26 | 1.368 (5) |
| C7—H7 | 0.9300 | C25—C30 | 1.379 (5) |
| C8—C9 | 1.429 (5) | C26—C27 | 1.382 (6) |
| C8—H8 | 0.9300 | C26—H26 | 0.9300 |
| C9—C10 | 1.401 (5) | C27—C28 | 1.360 (7) |
| C9—C14 | 1.461 (5) | C27—H27 | 0.9300 |
| C10—C11 | 1.414 (5) | C28—C29 | 1.344 (8) |
| C11—C12 | 1.346 (5) | C28—H28 | 0.9300 |
| C11—H11 | 0.9300 | C29—C30 | 1.397 (7) |
| C12—C13 | 1.413 (6) | C29—H29 | 0.9300 |
| C12—H12 | 0.9300 | C30—H30 | 0.9300 |
| O3—Sn1—C19 | 94.31 (12) | C18—C13—C14 | 119.4 (4) |
| O3—Sn1—C25 | 99.45 (13) | C12—C13—C14 | 119.6 (3) |
| C19—Sn1—C25 | 123.88 (13) | C15—C14—C13 | 117.2 (3) |
| O3—Sn1—O1 | 155.42 (10) | C15—C14—C9 | 124.3 (3) |
| C19—Sn1—O1 | 93.27 (12) | C13—C14—C9 | 118.4 (3) |
| C25—Sn1—O1 | 95.61 (13) | C16—C15—C14 | 122.2 (4) |
| O3—Sn1—N2 | 82.61 (10) | C16—C15—H15 | 118.9 |
| C19—Sn1—N2 | 122.65 (12) | C14—C15—H15 | 118.9 |
| C25—Sn1—N2 | 113.00 (13) | C15—C16—C17 | 120.7 (4) |
| O1—Sn1—N2 | 73.63 (10) | C15—C16—H16 | 119.6 |
| C1—N1—N2 | 112.1 (3) | C17—C16—H16 | 119.6 |
| C8—N2—N1 | 115.9 (3) | C18—C17—C16 | 119.0 (4) |
| C8—N2—Sn1 | 128.2 (2) | C18—C17—H17 | 120.5 |
| N1—N2—Sn1 | 115.7 (2) | C16—C17—H17 | 120.5 |
| C1—O1—Sn1 | 115.0 (2) | C17—C18—C13 | 121.4 (4) |
| C3—O2—H2 | 109.5 | C17—C18—H18 | 119.3 |
| C10—O3—Sn1 | 133.8 (2) | C13—C18—H18 | 119.3 |
| O1—C1—N1 | 123.6 (3) | C20—C19—C24 | 117.7 (4) |
| O1—C1—C2 | 117.9 (3) | C20—C19—Sn1 | 122.6 (3) |
| N1—C1—C2 | 118.6 (3) | C24—C19—Sn1 | 119.7 (3) |
| C3—C2—C7 | 118.0 (3) | C21—C20—C19 | 120.6 (4) |
| C3—C2—C1 | 122.9 (3) | C21—C20—H20 | 119.7 |
| C7—C2—C1 | 119.1 (4) | C19—C20—H20 | 119.7 |
| O2—C3—C4 | 117.6 (4) | C22—C21—C20 | 120.5 (4) |
| O2—C3—C2 | 122.6 (3) | C22—C21—H21 | 119.8 |
| C4—C3—C2 | 119.9 (4) | C20—C21—H21 | 119.8 |
| C5—C4—C3 | 120.2 (5) | C23—C22—C21 | 119.9 (5) |
| C5—C4—H4 | 119.9 | C23—C22—H22 | 120.1 |
| C3—C4—H4 | 119.9 | C21—C22—H22 | 120.1 |
| C6—C5—C4 | 120.8 (4) | C22—C23—C24 | 120.0 (4) |
| C6—C5—H5 | 119.6 | C22—C23—H23 | 120.0 |
| C4—C5—H5 | 119.6 | C24—C23—H23 | 120.0 |
| C5—C6—C7 | 118.9 (5) | C23—C24—C19 | 121.3 (4) |
| C5—C6—H6 | 120.5 | C23—C24—H24 | 119.3 |
| C7—C6—H6 | 120.5 | C19—C24—H24 | 119.3 |
| C6—C7—C2 | 122.2 (5) | C26—C25—C30 | 117.7 (4) |
| C6—C7—H7 | 118.9 | C26—C25—Sn1 | 120.3 (3) |
| C2—C7—H7 | 118.9 | C30—C25—Sn1 | 121.9 (3) |
| N2—C8—C9 | 127.4 (3) | C25—C26—C27 | 121.4 (5) |
| N2—C8—H8 | 116.3 | C25—C26—H26 | 119.3 |
| C9—C8—H8 | 116.3 | C27—C26—H26 | 119.3 |
| C10—C9—C8 | 122.0 (3) | C28—C27—C26 | 120.0 (5) |
| C10—C9—C14 | 119.2 (3) | C28—C27—H27 | 120.0 |
| C8—C9—C14 | 118.8 (3) | C26—C27—H27 | 120.0 |
| O3—C10—C9 | 124.0 (3) | C29—C28—C27 | 120.1 (5) |
| O3—C10—C11 | 115.9 (3) | C29—C28—H28 | 120.0 |
| C9—C10—C11 | 120.0 (3) | C27—C28—H28 | 120.0 |
| C12—C11—C10 | 121.0 (4) | C28—C29—C30 | 120.3 (5) |
| C12—C11—H11 | 119.5 | C28—C29—H29 | 119.9 |
| C10—C11—H11 | 119.5 | C30—C29—H29 | 119.9 |
| C11—C12—C13 | 121.8 (4) | C25—C30—C29 | 120.5 (5) |
| C11—C12—H12 | 119.1 | C25—C30—H30 | 119.7 |
| C13—C12—H12 | 119.1 | C29—C30—H30 | 119.7 |
| C18—C13—C12 | 121.0 (4) | ||
| C1—N1—N2—C8 | 175.7 (3) | C11—C12—C13—C18 | −179.6 (4) |
| C1—N1—N2—Sn1 | −0.9 (4) | C11—C12—C13—C14 | 1.3 (6) |
| O3—Sn1—N2—C8 | 11.5 (3) | C18—C13—C14—C15 | 2.1 (6) |
| C19—Sn1—N2—C8 | 101.9 (3) | C12—C13—C14—C15 | −178.8 (4) |
| C25—Sn1—N2—C8 | −85.7 (3) | C18—C13—C14—C9 | −178.8 (4) |
| O1—Sn1—N2—C8 | −174.9 (3) | C12—C13—C14—C9 | 0.3 (6) |
| O3—Sn1—N2—N1 | −172.4 (2) | C10—C9—C14—C15 | 177.3 (4) |
| C19—Sn1—N2—N1 | −82.1 (3) | C8—C9—C14—C15 | −4.9 (6) |
| C25—Sn1—N2—N1 | 90.4 (3) | C10—C9—C14—C13 | −1.8 (5) |
| O1—Sn1—N2—N1 | 1.2 (2) | C8—C9—C14—C13 | 176.0 (3) |
| O3—Sn1—O1—C1 | 14.0 (5) | C13—C14—C15—C16 | −1.8 (7) |
| C19—Sn1—O1—C1 | 121.8 (3) | C9—C14—C15—C16 | 179.2 (4) |
| C25—Sn1—O1—C1 | −113.7 (3) | C14—C15—C16—C17 | 0.7 (8) |
| N2—Sn1—O1—C1 | −1.3 (3) | C15—C16—C17—C18 | 0.0 (8) |
| C19—Sn1—O3—C10 | −137.9 (3) | C16—C17—C18—C13 | 0.4 (8) |
| C25—Sn1—O3—C10 | 96.7 (3) | C12—C13—C18—C17 | 179.4 (5) |
| O1—Sn1—O3—C10 | −30.3 (5) | C14—C13—C18—C17 | −1.5 (7) |
| N2—Sn1—O3—C10 | −15.5 (3) | O3—Sn1—C19—C20 | 17.9 (3) |
| Sn1—O1—C1—N1 | 1.4 (5) | C25—Sn1—C19—C20 | 122.4 (3) |
| Sn1—O1—C1—C2 | −178.6 (3) | O1—Sn1—C19—C20 | −138.7 (3) |
| N2—N1—C1—O1 | −0.3 (5) | N2—Sn1—C19—C20 | −66.0 (3) |
| N2—N1—C1—C2 | 179.7 (3) | O3—Sn1—C19—C24 | −162.6 (3) |
| O1—C1—C2—C3 | −170.6 (4) | C25—Sn1—C19—C24 | −58.2 (3) |
| N1—C1—C2—C3 | 9.4 (6) | O1—Sn1—C19—C24 | 40.8 (3) |
| O1—C1—C2—C7 | 7.9 (6) | N2—Sn1—C19—C24 | 113.5 (3) |
| N1—C1—C2—C7 | −172.1 (4) | C24—C19—C20—C21 | −1.6 (6) |
| C7—C2—C3—O2 | 179.7 (4) | Sn1—C19—C20—C21 | 177.9 (3) |
| C1—C2—C3—O2 | −1.8 (6) | C19—C20—C21—C22 | 2.3 (7) |
| C7—C2—C3—C4 | −0.5 (6) | C20—C21—C22—C23 | −0.9 (7) |
| C1—C2—C3—C4 | 178.0 (4) | C21—C22—C23—C24 | −1.2 (7) |
| O2—C3—C4—C5 | 179.3 (5) | C22—C23—C24—C19 | 1.9 (7) |
| C2—C3—C4—C5 | −0.6 (7) | C20—C19—C24—C23 | −0.5 (6) |
| C3—C4—C5—C6 | 1.9 (8) | Sn1—C19—C24—C23 | 180.0 (3) |
| C4—C5—C6—C7 | −2.1 (9) | O3—Sn1—C25—C26 | 37.8 (3) |
| C5—C6—C7—C2 | 1.1 (9) | C19—Sn1—C25—C26 | −64.0 (4) |
| C3—C2—C7—C6 | 0.2 (7) | O1—Sn1—C25—C26 | −161.7 (3) |
| C1—C2—C7—C6 | −178.4 (5) | N2—Sn1—C25—C26 | 123.7 (3) |
| N1—N2—C8—C9 | 179.4 (3) | O3—Sn1—C25—C30 | −142.1 (3) |
| Sn1—N2—C8—C9 | −4.6 (6) | C19—Sn1—C25—C30 | 116.1 (3) |
| N2—C8—C9—C10 | −5.8 (6) | O1—Sn1—C25—C30 | 18.4 (3) |
| N2—C8—C9—C14 | 176.5 (4) | N2—Sn1—C25—C30 | −56.2 (4) |
| Sn1—O3—C10—C9 | 11.6 (6) | C30—C25—C26—C27 | −0.4 (7) |
| Sn1—O3—C10—C11 | −169.6 (3) | Sn1—C25—C26—C27 | 179.7 (4) |
| C8—C9—C10—O3 | 2.8 (6) | C25—C26—C27—C28 | 1.4 (8) |
| C14—C9—C10—O3 | −179.5 (3) | C26—C27—C28—C29 | −1.0 (8) |
| C8—C9—C10—C11 | −176.0 (3) | C27—C28—C29—C30 | −0.3 (8) |
| C14—C9—C10—C11 | 1.7 (5) | C26—C25—C30—C29 | −0.9 (7) |
| O3—C10—C11—C12 | −179.0 (4) | Sn1—C25—C30—C29 | 179.0 (4) |
| C9—C10—C11—C12 | −0.2 (6) | C28—C29—C30—C25 | 1.2 (8) |
| C10—C11—C12—C13 | −1.4 (6) |
| Sn1—O1 | 2.121 (2) | Sn1—C19 | 2.106 (4) |
| Sn1—O3 | 2.061 (2) | Sn1—C25 | 2.113 (4) |
| Sn1—N2 | 2.154 (3) |
We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.
Chen, S.-W., Yin, H.-D. & Wang, D.-Q. (2006). Acta Cryst. E62, m28–m29.
Sanderson, R. T. (1967). Inorganic Chemistry, p. 74. New York: Reinhold.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Yearwood, B., Parkin, S. & Atwood, D. A. (2002). Inorg. Chim. Acta, 333, 124–131.
The molecular structure of the title compound is shown in Fig. 1. The SnIV atom is five-coordinated by two O atoms, two C atoms and one N atom. The distortion around the SnIV atom is a result of the constraints imposed by the Sn1–N2–N1–C1–O1 and Sn1–N2–C8–C9–C10–O3 rings. The dihedral angles between the two benzene rings (C19 to C24 and C25 to C30) and the O3–Sn1–N2 plane are 61.5 (1) and 67.2 (1)°, respectively. The Sn1—N2 distance is 2.154 (3) Å, close to the sum of the covalent radii (2.15 Å; Sanderson, 1967), indicating a strong Sn—N interaction. The O atoms coordinate to the Sn atom with one shorter and one longer Sn—O bond. Very similar structural parameters were observed in the compound studied by Yearwood et al. (2002). The angles at Sn1 confirm that the complex has a distorted trigonal-bipyramidal geometry.