metal-organic compounds
[N′-(3-Methoxy-2-oxidobenzylidene)nicotinohydrazidato]dimethyltin(IV)
aDepartment of Chemistry and Chemical Engineering, Jining University, Shandong 273155, People's Republic of China
*Correspondence e-mail: zhongjungao@sina.com
In the title complex, [Sn(CH3)2(C14H11N3O3)], the Sn atom is in a distorted trigonal-bipyramidal coordination, with Sn—O distances of 2.138 (2) and 2.176 (2) Å. The dihedral angles between the two chelated benzene rings and the O—Sn—N group are 71.73 (9) and 83.30 (9)°.
Related literature
For covalent radii, see: Sanderson (1967). For bond-lengh data, see: Yang et al. (1999). For a related structure, see: Yearwood et al. (2002).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); data reduction: SAINT; 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.
Supporting information
10.1107/S160053680903726X/kp2231sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680903726X/kp2231Isup2.hkl
A mixture of dimethyltin oxide (0.3295 g, 2.0 mmol) and 3-methoxy-2-oxideobenzaldehyde(3-pyridyl)methyl-hydrazone (0.5420 g, 2.0 mmol) in methanol (50 ml) was heated under reflux for 6 h. The obtained clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/ethanol (1:1) to yield blocks of (I). Yield 0.5936 g, 71%, m.p. 453 K, analysis, calculated for C16H17N3O3Sn: C 45.97, H, 4.10; N 10.06%; found: C 46.02, H 4.05, N, 10.09%.
H atoms were positioned with idealized geometry with C—H = 0.93 Å for aromatic H atomds and 0.96 Å for methyl H atoms and were constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(for methyl groups).
Data collection: SMART (Siemens, 1996); cell
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 complex with 30% displacement ellipsoids (H atoms omitted for clarity). |
[Sn(CH3)2(C14H11N3O3)] | F(000) = 1664 |
Mr = 418.02 | Dx = 1.689 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4244 reflections |
a = 26.121 (8) Å | θ = 2.2–27.6° |
b = 9.795 (3) Å | µ = 1.57 mm−1 |
c = 13.227 (4) Å | T = 298 K |
β = 103.666 (4)° | Block, yellow |
V = 3288.4 (17) Å3 | 0.35 × 0.16 × 0.12 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 3574 independent reflections |
Radiation source: fine-focus sealed tube | 3115 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 27.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −33→20 |
Tmin = 0.609, Tmax = 0.834 | k = −12→12 |
9367 measured reflections | l = −13→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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.5213P] where P = (Fo2 + 2Fc2)/3 |
3574 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
[Sn(CH3)2(C14H11N3O3)] | V = 3288.4 (17) Å3 |
Mr = 418.02 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 26.121 (8) Å | µ = 1.57 mm−1 |
b = 9.795 (3) Å | T = 298 K |
c = 13.227 (4) Å | 0.35 × 0.16 × 0.12 mm |
β = 103.666 (4)° |
Bruker SMART CCD area-detector diffractometer | 3574 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3115 reflections with I > 2σ(I) |
Tmin = 0.609, Tmax = 0.834 | Rint = 0.023 |
9367 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.48 e Å−3 |
3574 reflections | Δρmin = −0.54 e Å−3 |
211 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 | −0.17768 (17) | −0.0742 (5) | −0.0099 (5) | 0.112 (2) | |
H1A | −0.1913 | −0.0622 | 0.0509 | 0.169* | |
H1B | −0.1729 | −0.1697 | −0.0208 | 0.169* | |
H1C | −0.2021 | −0.0368 | −0.0693 | 0.169* | |
C2 | −0.12735 (12) | 0.1271 (3) | 0.0369 (2) | 0.0486 (7) | |
C3 | −0.17073 (12) | 0.1957 (3) | 0.0522 (3) | 0.0543 (8) | |
H3 | −0.2031 | 0.1515 | 0.0391 | 0.065* | |
C4 | −0.16700 (14) | 0.3308 (3) | 0.0870 (3) | 0.0598 (9) | |
H4 | −0.1966 | 0.3761 | 0.0973 | 0.072* | |
C5 | −0.11962 (12) | 0.3952 (3) | 0.1057 (3) | 0.0530 (7) | |
H5 | −0.1171 | 0.4852 | 0.1286 | 0.064* | |
C6 | −0.07437 (12) | 0.3282 (3) | 0.0910 (2) | 0.0450 (7) | |
C7 | −0.07714 (12) | 0.1931 (3) | 0.0542 (2) | 0.0441 (7) | |
C8 | −0.02708 (12) | 0.4074 (3) | 0.1159 (2) | 0.0461 (6) | |
H8 | −0.0301 | 0.4944 | 0.1421 | 0.055* | |
C9 | 0.10299 (11) | 0.4315 (3) | 0.1225 (2) | 0.0453 (7) | |
C10 | 0.14890 (11) | 0.5246 (3) | 0.1563 (2) | 0.0458 (7) | |
C11 | 0.14558 (15) | 0.6528 (3) | 0.1969 (3) | 0.0579 (8) | |
H11 | 0.1133 | 0.6872 | 0.2032 | 0.069* | |
C12 | 0.19100 (16) | 0.7297 (4) | 0.2282 (3) | 0.0701 (10) | |
H12 | 0.1898 | 0.8172 | 0.2549 | 0.084* | |
C13 | 0.23784 (17) | 0.6734 (4) | 0.2190 (3) | 0.0701 (11) | |
H13 | 0.2683 | 0.7251 | 0.2416 | 0.084* | |
C14 | 0.19835 (12) | 0.4796 (3) | 0.1490 (3) | 0.0563 (8) | |
H14 | 0.2006 | 0.3938 | 0.1202 | 0.068* | |
C15 | 0.07460 (13) | 0.0606 (3) | 0.1813 (2) | 0.0564 (8) | |
H15A | 0.0728 | −0.0342 | 0.1625 | 0.085* | |
H15B | 0.0544 | 0.0760 | 0.2323 | 0.085* | |
H15C | 0.1106 | 0.0858 | 0.2099 | 0.085* | |
C16 | 0.03460 (15) | 0.1988 (3) | −0.1120 (3) | 0.0562 (8) | |
H16A | 0.0649 | 0.2438 | −0.1258 | 0.084* | |
H16B | 0.0036 | 0.2518 | −0.1405 | 0.084* | |
H16C | 0.0310 | 0.1100 | −0.1435 | 0.084* | |
N1 | 0.05804 (9) | 0.4727 (2) | 0.1381 (2) | 0.0477 (6) | |
N2 | 0.01913 (9) | 0.3731 (3) | 0.10640 (18) | 0.0445 (5) | |
N3 | 0.24269 (11) | 0.5509 (3) | 0.1802 (3) | 0.0683 (8) | |
O1 | −0.12845 (9) | −0.0056 (3) | 0.0043 (2) | 0.0690 (7) | |
O2 | −0.03632 (8) | 0.1225 (2) | 0.03858 (18) | 0.0546 (5) | |
O3 | 0.11123 (10) | 0.3162 (2) | 0.0820 (2) | 0.0604 (6) | |
Sn1 | 0.043848 (7) | 0.17888 (2) | 0.049245 (14) | 0.04388 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.066 (3) | 0.083 (3) | 0.202 (6) | −0.031 (2) | 0.060 (3) | −0.070 (3) |
C2 | 0.0429 (16) | 0.0581 (18) | 0.0459 (16) | −0.0086 (14) | 0.0129 (12) | −0.0022 (14) |
C3 | 0.0378 (16) | 0.072 (2) | 0.0542 (19) | −0.0055 (14) | 0.0135 (14) | 0.0008 (15) |
C4 | 0.0459 (18) | 0.069 (2) | 0.069 (2) | 0.0046 (15) | 0.0219 (16) | −0.0008 (16) |
C5 | 0.0518 (18) | 0.0535 (18) | 0.0568 (19) | 0.0003 (14) | 0.0190 (14) | 0.0026 (15) |
C6 | 0.0419 (16) | 0.0540 (17) | 0.0397 (15) | −0.0042 (12) | 0.0107 (12) | 0.0063 (12) |
C7 | 0.0394 (15) | 0.0581 (18) | 0.0354 (14) | −0.0030 (12) | 0.0103 (11) | 0.0039 (12) |
C8 | 0.0472 (17) | 0.0458 (15) | 0.0459 (16) | −0.0028 (13) | 0.0120 (12) | 0.0027 (13) |
C9 | 0.0451 (16) | 0.0492 (16) | 0.0418 (15) | −0.0110 (13) | 0.0104 (12) | 0.0012 (13) |
C10 | 0.0479 (16) | 0.0466 (16) | 0.0421 (15) | −0.0124 (13) | 0.0091 (12) | 0.0037 (13) |
C11 | 0.061 (2) | 0.0536 (18) | 0.061 (2) | −0.0123 (15) | 0.0173 (16) | −0.0053 (15) |
C12 | 0.082 (3) | 0.0534 (19) | 0.076 (3) | −0.023 (2) | 0.022 (2) | −0.0120 (19) |
C13 | 0.057 (2) | 0.079 (3) | 0.071 (3) | −0.0297 (18) | 0.0076 (18) | −0.0001 (19) |
C14 | 0.0514 (18) | 0.0535 (18) | 0.062 (2) | −0.0115 (15) | 0.0101 (15) | −0.0008 (16) |
C15 | 0.060 (2) | 0.061 (2) | 0.0445 (17) | −0.0025 (15) | 0.0053 (14) | 0.0008 (14) |
C16 | 0.075 (2) | 0.0510 (18) | 0.0452 (18) | −0.0102 (16) | 0.0203 (16) | −0.0036 (14) |
N1 | 0.0450 (14) | 0.0442 (13) | 0.0535 (15) | −0.0077 (11) | 0.0107 (11) | −0.0006 (11) |
N2 | 0.0445 (14) | 0.0462 (13) | 0.0426 (13) | −0.0091 (11) | 0.0100 (10) | −0.0005 (11) |
N3 | 0.0507 (17) | 0.0673 (19) | 0.085 (2) | −0.0174 (14) | 0.0116 (14) | −0.0038 (16) |
O1 | 0.0457 (12) | 0.0708 (15) | 0.0958 (19) | −0.0155 (11) | 0.0277 (12) | −0.0276 (14) |
O2 | 0.0400 (11) | 0.0565 (13) | 0.0689 (15) | −0.0080 (10) | 0.0162 (10) | −0.0079 (11) |
O3 | 0.0509 (14) | 0.0569 (14) | 0.0793 (18) | −0.0155 (10) | 0.0269 (12) | −0.0220 (11) |
Sn1 | 0.04134 (14) | 0.04977 (15) | 0.04093 (14) | −0.01097 (8) | 0.01049 (9) | −0.00053 (8) |
C1—O1 | 1.423 (4) | C10—C14 | 1.390 (4) |
C1—H1A | 0.9600 | C11—C12 | 1.383 (5) |
C1—H1B | 0.9600 | C11—H11 | 0.9300 |
C1—H1C | 0.9600 | C12—C13 | 1.374 (6) |
C2—O1 | 1.367 (4) | C12—H12 | 0.9300 |
C2—C3 | 1.373 (5) | C13—N3 | 1.323 (5) |
C2—C7 | 1.431 (4) | C13—H13 | 0.9300 |
C3—C4 | 1.397 (4) | C14—N3 | 1.332 (4) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.359 (5) | C15—Sn1 | 2.092 (3) |
C4—H4 | 0.9300 | C15—H15A | 0.9600 |
C5—C6 | 1.405 (4) | C15—H15B | 0.9600 |
C5—H5 | 0.9300 | C15—H15C | 0.9600 |
C6—C7 | 1.406 (4) | C16—Sn1 | 2.098 (3) |
C6—C8 | 1.430 (4) | C16—H16A | 0.9600 |
C7—O2 | 1.327 (4) | C16—H16B | 0.9600 |
C8—N2 | 1.287 (4) | C16—H16C | 0.9600 |
C8—H8 | 0.9300 | N1—N2 | 1.400 (3) |
C9—O3 | 1.290 (3) | N2—Sn1 | 2.200 (3) |
C9—N1 | 1.304 (4) | O2—Sn1 | 2.138 (2) |
C9—C10 | 1.489 (4) | O3—Sn1 | 2.176 (2) |
C10—C11 | 1.377 (4) | ||
O1—C1—H1A | 109.5 | C11—C12—H12 | 120.8 |
O1—C1—H1B | 109.5 | N3—C13—C12 | 124.6 (3) |
H1A—C1—H1B | 109.5 | N3—C13—H13 | 117.7 |
O1—C1—H1C | 109.5 | C12—C13—H13 | 117.7 |
H1A—C1—H1C | 109.5 | N3—C14—C10 | 124.5 (3) |
H1B—C1—H1C | 109.5 | N3—C14—H14 | 117.7 |
O1—C2—C3 | 123.7 (3) | C10—C14—H14 | 117.7 |
O1—C2—C7 | 115.5 (3) | Sn1—C15—H15A | 109.5 |
C3—C2—C7 | 120.8 (3) | Sn1—C15—H15B | 109.5 |
C2—C3—C4 | 121.1 (3) | H15A—C15—H15B | 109.5 |
C2—C3—H3 | 119.4 | Sn1—C15—H15C | 109.5 |
C4—C3—H3 | 119.4 | H15A—C15—H15C | 109.5 |
C5—C4—C3 | 119.3 (3) | H15B—C15—H15C | 109.5 |
C5—C4—H4 | 120.4 | Sn1—C16—H16A | 109.5 |
C3—C4—H4 | 120.4 | Sn1—C16—H16B | 109.5 |
C4—C5—C6 | 121.2 (3) | H16A—C16—H16B | 109.5 |
C4—C5—H5 | 119.4 | Sn1—C16—H16C | 109.5 |
C6—C5—H5 | 119.4 | H16A—C16—H16C | 109.5 |
C5—C6—C7 | 120.8 (3) | H16B—C16—H16C | 109.5 |
C5—C6—C8 | 115.1 (3) | C9—N1—N2 | 110.7 (2) |
C7—C6—C8 | 124.2 (3) | C8—N2—N1 | 114.8 (2) |
O2—C7—C6 | 124.5 (3) | C8—N2—Sn1 | 128.1 (2) |
O2—C7—C2 | 118.7 (3) | N1—N2—Sn1 | 117.03 (18) |
C6—C7—C2 | 116.8 (3) | C13—N3—C14 | 116.1 (3) |
N2—C8—C6 | 127.9 (3) | C2—O1—C1 | 116.2 (3) |
N2—C8—H8 | 116.0 | C7—O2—Sn1 | 131.74 (19) |
C6—C8—H8 | 116.0 | C9—O3—Sn1 | 114.66 (19) |
O3—C9—N1 | 125.6 (3) | C15—Sn1—C16 | 146.08 (14) |
O3—C9—C10 | 117.4 (3) | C15—Sn1—O2 | 95.11 (11) |
N1—C9—C10 | 117.0 (3) | C16—Sn1—O2 | 94.66 (12) |
C11—C10—C14 | 117.5 (3) | C15—Sn1—O3 | 92.46 (12) |
C11—C10—C9 | 123.8 (3) | C16—Sn1—O3 | 92.19 (12) |
C14—C10—C9 | 118.7 (3) | O2—Sn1—O3 | 155.02 (9) |
C10—C11—C12 | 119.0 (4) | C15—Sn1—N2 | 106.13 (11) |
C10—C11—H11 | 120.5 | C16—Sn1—N2 | 107.23 (11) |
C12—C11—H11 | 120.5 | O2—Sn1—N2 | 83.30 (9) |
C13—C12—C11 | 118.3 (4) | O3—Sn1—N2 | 71.73 (9) |
C13—C12—H12 | 120.8 | ||
O1—C2—C3—C4 | 179.1 (3) | C6—C8—N2—N1 | −179.5 (3) |
C7—C2—C3—C4 | −1.4 (5) | C6—C8—N2—Sn1 | −0.4 (4) |
C2—C3—C4—C5 | 0.2 (5) | C9—N1—N2—C8 | −177.8 (3) |
C3—C4—C5—C6 | −0.3 (5) | C9—N1—N2—Sn1 | 3.0 (3) |
C4—C5—C6—C7 | 1.5 (5) | C12—C13—N3—C14 | −0.2 (6) |
C4—C5—C6—C8 | −178.7 (3) | C10—C14—N3—C13 | −1.2 (5) |
C5—C6—C7—O2 | −179.7 (3) | C3—C2—O1—C1 | −2.4 (5) |
C8—C6—C7—O2 | 0.5 (5) | C7—C2—O1—C1 | 178.0 (4) |
C5—C6—C7—C2 | −2.5 (4) | C6—C7—O2—Sn1 | −5.1 (4) |
C8—C6—C7—C2 | 177.7 (3) | C2—C7—O2—Sn1 | 177.7 (2) |
O1—C2—C7—O2 | −0.5 (4) | N1—C9—O3—Sn1 | −4.5 (4) |
C3—C2—C7—O2 | 179.9 (3) | C10—C9—O3—Sn1 | 174.16 (19) |
O1—C2—C7—C6 | −177.9 (3) | C7—O2—Sn1—C15 | 110.8 (3) |
C3—C2—C7—C6 | 2.4 (4) | C7—O2—Sn1—C16 | −101.7 (3) |
C5—C6—C8—N2 | −177.5 (3) | C7—O2—Sn1—O3 | 3.7 (4) |
C7—C6—C8—N2 | 2.3 (5) | C7—O2—Sn1—N2 | 5.1 (3) |
O3—C9—C10—C11 | 177.3 (3) | C9—O3—Sn1—C15 | −102.0 (2) |
N1—C9—C10—C11 | −3.9 (4) | C9—O3—Sn1—C16 | 111.6 (2) |
O3—C9—C10—C14 | −4.0 (4) | C9—O3—Sn1—O2 | 5.6 (4) |
N1—C9—C10—C14 | 174.7 (3) | C9—O3—Sn1—N2 | 4.2 (2) |
C14—C10—C11—C12 | −0.1 (5) | C8—N2—Sn1—C15 | −95.7 (3) |
C9—C10—C11—C12 | 178.5 (3) | N1—N2—Sn1—C15 | 83.4 (2) |
C10—C11—C12—C13 | −1.1 (6) | C8—N2—Sn1—C16 | 90.5 (3) |
C11—C12—C13—N3 | 1.3 (6) | N1—N2—Sn1—C16 | −90.4 (2) |
C11—C10—C14—N3 | 1.3 (5) | C8—N2—Sn1—O2 | −2.3 (2) |
C9—C10—C14—N3 | −177.4 (3) | N1—N2—Sn1—O2 | 176.8 (2) |
O3—C9—N1—N2 | 1.0 (4) | C8—N2—Sn1—O3 | 177.0 (3) |
C10—C9—N1—N2 | −177.6 (2) | N1—N2—Sn1—O3 | −3.86 (19) |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)2(C14H11N3O3)] |
Mr | 418.02 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 26.121 (8), 9.795 (3), 13.227 (4) |
β (°) | 103.666 (4) |
V (Å3) | 3288.4 (17) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.57 |
Crystal size (mm) | 0.35 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.609, 0.834 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9367, 3574, 3115 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.087, 1.00 |
No. of reflections | 3574 |
No. of parameters | 211 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.54 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
C15—Sn1 | 2.092 (3) | O2—Sn1 | 2.138 (2) |
C16—Sn1 | 2.098 (3) | O3—Sn1 | 2.176 (2) |
N2—Sn1 | 2.200 (3) |
Acknowledgements
We acknowledge the financial support of the Jining University Science Foundation and the State Key Laboratory of Crystal Materials, Shandong University.
References
Sanderson, R. T. (1967). Inorganic Chemistry, p. 74. New York: Reinhold. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yang, Z. Y., Yang, R. D. & Yu, K. B. (1999). Acta Chim. Sin. 57, 236–243. CAS Google Scholar
Yearwood, B., Parkin, C. H. & Atwood, D. A. (2002). Inorg. Chim. Acta, 333, 124–131. Web of Science CSD CrossRef CAS Google Scholar
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In the structure of the title compound, (I), (Fig. 1) the Sn1 atom is in a distored trigonal-bipyramidal coordination formed by a tridentate ligand of the azomethine N atom, the hydroxyl O atom and the carbonyl O atom (Table 1). The dihedral angles between the two chelated benzene rings: O2—Sn1—N2 and O3—Sn1—N2 are 83.30 (9) and 71.73 (9)°, respectively. The Sn atom is coordinated in distorted trigonal-bipyramidal arrangement with O2 and O3 located in the axial positions [O2—Sn1—O3 = 155.02 (9)°] and the C15, C16 and N2 in the equatorial positions. The sum of the C15—Sn1—C16 [146.08 (14)], C15—Sn1—N2 [106.13 (11)] and C16—Sn1—N2 [107.23 (11)°] bond angles is 359.44°, indicating approximate co-planarity for these atoms. Comparing the length of CN 1.270Å and C—N 1.470 Å, both bonds, C8—N2 (1.287 (4) Å) and C9—N1 (1.304 (4) Å) should be CN. The N1—N2 bond (1.400 (3) Å) is a single-bond (Yang et al., 1999). The Sn1—N2 distance is close to the sum of the covalent radii of 2.15Å (Sanderson, 1967), indicating a strong Sn—N interaction. Very similar structural parameters were observed in the compound studied by Yearwood et al. (2002).