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In the title complex, [Sn(C6H5)2(C17H11N3O2)], the Sn atom is in a distorted trigonal-bipyramidal geometry, with Sn-O distances in the range 2.074 (3)-2.141 (3) Å. The dihedral angles between the two chelated benzene rings and the O(naphthyl oxide)-Sn-N group are 75.8 (1) and 50.6 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038523/sg6041sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038523/sg6041Isup2.hkl
Contains datablock I

CCDC reference: 288680

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.033
  • wR factor = 0.083
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.84 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C18 -C23 1.37 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H7 .. H10 .. 1.97 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The structure of the title molecule, (I), in Fig. 1 shows that the complex is a monomer in which the Sn atom adopts a five-coordinate geometry, being coordinated by two O atoms, two C atoms and one N atom. The Schiff base is coordinated to the Sn atom as a tridentate ligand via the azomethine N atom, the hydroxyl O atom and the carbonyl O atom. Thus, the C—N—N—C chain can indicate [What? Text missing. Conjugation?] by the intermediate C7—N3 [1.309 (4) Å], N3—N2 [1.403 (4) Å] and N2—C6 [1.296 (4) Å] bonds. The Sn1—N3 distance is 2.141 (3) Å, which is close to the sum of the non-polar covalent radii (2.15 Å; Sanderson, 1967), indicating a strong Sn—N interaction. The O atoms coordinate to the Sn atom with one shorter Sn—O bond [Sn1—O1 2.117 (3) Å] and one longer Sn—O bond [Sn1—O2 2.074 (3) Å]. These lengths are similar to the Sn1—C24 and Sn1—C18 bonds [2.109 (4) and 2.113 (4) Å, respectively]. Very similar structural parameters were observed in the compound studied by Yearwood et al. (2002). The O2—Sn1—C24, O2—Sn1—C18 and C24—Sn1—C18 angles are 96.74 (14), 95.03 (14) and 120.33 (15)°, respectively, confirming that the complex has a distorted trigonal–bipyramidal configuration.

Experimental top

The synthesis of (I) was carried out under a nitrogen atmosphere using standard Schlenk techniques. The Schiff base (0.1165 g, 4 mmol) was added to a mixture of ethanol and benzene (1:3 v/v, 30 ml) with sodium ethoxide (0.272 g, 4 mmol). The mixture was stirred for 0.5 h and then Ph2SnCl2 (0.1376 g, 4 mmol) was added and the mixture stirred for 10 h under reflux. After cooling to room temperature, the mixture was filtered and evaporated to dryness. The resulting solid, (I), was then recrystallized from dichloromethane–hexane (3:1, v/v) (m.p. 515–516 K). Analysis, calculated for C29H21N3O2Sn: C 61.95, H 3.76, N 7.47%; found: C 61.73, N 3.65, N 7.58%.

Refinement top

All H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distances of 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 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.

Figures top
[Figure 1] Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the title complex.
[2-Oxido-1-naphthaldehyde oxido(4-pyridyl)methylhydrazone]diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C17H11N3O2)]F(000) = 1128
Mr = 562.18Dx = 1.556 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.283 (4) ÅCell parameters from 4361 reflections
b = 21.060 (8) Åθ = 2.4–24.7°
c = 11.984 (5) ŵ = 1.10 mm1
β = 112.380 (5)°T = 298 K
V = 2399.9 (15) Å3Block, orange
Z = 40.49 × 0.47 × 0.43 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
4205 independent reflections
Radiation source: fine-focus sealed tube3087 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.616, Tmax = 0.650k = 2523
12415 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0299P)2 + 1.5741P]
where P = (Fo2 + 2Fc2)/3
4205 reflections(Δ/σ)max < 0.001
316 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.48 e Å3
Crystal data top
[Sn(C6H5)2(C17H11N3O2)]V = 2399.9 (15) Å3
Mr = 562.18Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.283 (4) ŵ = 1.10 mm1
b = 21.060 (8) ÅT = 298 K
c = 11.984 (5) Å0.49 × 0.47 × 0.43 mm
β = 112.380 (5)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
4205 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3087 reflections with I > 2σ(I)
Tmin = 0.616, Tmax = 0.650Rint = 0.042
12415 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 1.03Δρmax = 0.63 e Å3
4205 reflectionsΔρmin = 0.48 e Å3
316 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.51000 (3)0.107422 (12)0.72358 (2)0.04583 (11)
N10.9571 (4)0.15598 (19)0.9366 (4)0.0785 (12)
N20.5352 (3)0.03155 (14)0.6719 (3)0.0462 (7)
N30.4402 (3)0.01913 (13)0.6316 (3)0.0403 (7)
O10.6587 (3)0.03852 (12)0.8235 (2)0.0582 (7)
O20.3226 (3)0.13979 (12)0.5944 (3)0.0573 (7)
C10.7509 (4)0.06501 (18)0.8241 (3)0.0453 (9)
C20.8545 (5)0.0545 (2)0.9364 (4)0.0712 (13)
H20.85700.01670.97740.085*
C30.9543 (6)0.1010 (3)0.9868 (5)0.0922 (18)
H31.02450.09281.06180.111*
C40.8573 (5)0.1651 (2)0.8280 (4)0.0649 (12)
H40.85780.20320.78890.078*
C50.7536 (4)0.12192 (18)0.7698 (4)0.0522 (10)
H50.68570.13130.69420.063*
C60.6416 (4)0.01642 (17)0.7690 (3)0.0425 (9)
C70.3216 (4)0.00568 (17)0.5429 (3)0.0427 (9)
H70.31180.03560.51330.051*
C80.2062 (4)0.04712 (17)0.4868 (3)0.0397 (8)
C90.0781 (4)0.02110 (18)0.3961 (3)0.0443 (9)
C100.0618 (4)0.0425 (2)0.3597 (4)0.0564 (11)
H100.13610.07060.39430.068*
C110.0617 (5)0.0644 (2)0.2738 (4)0.0678 (12)
H110.07050.10710.25200.081*
C120.1737 (5)0.0231 (3)0.2194 (4)0.0745 (14)
H120.25640.03780.16010.089*
C130.1620 (4)0.0379 (2)0.2527 (4)0.0678 (13)
H130.23790.06500.21670.081*
C140.0374 (4)0.0622 (2)0.3411 (3)0.0506 (10)
C150.0270 (4)0.1261 (2)0.3784 (4)0.0582 (11)
H150.10410.15270.34330.070*
C160.0905 (4)0.15009 (19)0.4627 (4)0.0520 (10)
H160.09290.19240.48540.062*
C170.2109 (4)0.11126 (17)0.5174 (3)0.0440 (9)
C180.4683 (4)0.14178 (18)0.8722 (4)0.0513 (10)
C190.5447 (6)0.1243 (3)0.9875 (4)0.0889 (17)
H190.61500.09391.00310.107*
C200.5189 (8)0.1513 (3)1.0820 (5)0.112 (2)
H200.57180.13841.16060.134*
C210.4195 (6)0.1956 (3)1.0629 (5)0.0838 (16)
H210.40490.21411.12760.101*
C220.3409 (6)0.2129 (3)0.9488 (5)0.0854 (16)
H220.27000.24290.93480.102*
C230.3641 (5)0.1870 (2)0.8534 (4)0.0717 (13)
H230.30940.19970.77530.086*
C240.6451 (4)0.15789 (17)0.6601 (4)0.0482 (10)
C250.6111 (5)0.1663 (2)0.5376 (4)0.0620 (11)
H250.52860.14890.48230.074*
C260.6994 (6)0.2007 (2)0.4973 (5)0.0799 (14)
H260.67590.20630.41490.096*
C270.8198 (6)0.2262 (2)0.5772 (7)0.0889 (17)
H270.87850.24940.54950.107*
C280.8552 (5)0.2179 (2)0.6981 (6)0.0828 (16)
H280.93800.23530.75270.099*
C290.7684 (4)0.1837 (2)0.7397 (4)0.0628 (12)
H290.79340.17800.82220.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03958 (17)0.03933 (16)0.05258 (18)0.00157 (12)0.01081 (12)0.00148 (13)
N10.070 (3)0.077 (3)0.072 (3)0.035 (2)0.008 (2)0.003 (2)
N20.0391 (18)0.0427 (18)0.0487 (19)0.0090 (14)0.0077 (16)0.0004 (15)
N30.0345 (17)0.0385 (17)0.0413 (17)0.0035 (13)0.0071 (14)0.0015 (13)
O10.0529 (17)0.0463 (16)0.0551 (17)0.0102 (13)0.0022 (14)0.0050 (13)
O20.0467 (17)0.0389 (15)0.0712 (19)0.0027 (12)0.0056 (15)0.0018 (14)
C10.041 (2)0.049 (2)0.043 (2)0.0060 (17)0.0124 (18)0.0042 (18)
C20.065 (3)0.065 (3)0.062 (3)0.022 (2)0.000 (2)0.009 (2)
C30.071 (3)0.098 (4)0.073 (3)0.039 (3)0.013 (3)0.006 (3)
C40.065 (3)0.057 (3)0.071 (3)0.018 (2)0.025 (3)0.000 (2)
C50.048 (2)0.056 (3)0.046 (2)0.0096 (19)0.010 (2)0.0010 (19)
C60.042 (2)0.040 (2)0.044 (2)0.0025 (16)0.0141 (19)0.0019 (17)
C70.041 (2)0.041 (2)0.044 (2)0.0012 (16)0.0132 (19)0.0004 (17)
C80.034 (2)0.045 (2)0.037 (2)0.0016 (16)0.0108 (17)0.0044 (17)
C90.039 (2)0.055 (2)0.038 (2)0.0009 (18)0.0145 (18)0.0057 (18)
C100.044 (2)0.062 (3)0.054 (3)0.003 (2)0.009 (2)0.003 (2)
C110.054 (3)0.072 (3)0.066 (3)0.008 (2)0.009 (2)0.009 (2)
C120.050 (3)0.097 (4)0.061 (3)0.014 (3)0.003 (2)0.002 (3)
C130.043 (3)0.086 (4)0.061 (3)0.003 (2)0.006 (2)0.016 (3)
C140.039 (2)0.063 (3)0.046 (2)0.0019 (19)0.0120 (19)0.013 (2)
C150.043 (2)0.066 (3)0.062 (3)0.015 (2)0.016 (2)0.020 (2)
C160.043 (2)0.048 (2)0.060 (3)0.0070 (18)0.015 (2)0.011 (2)
C170.037 (2)0.048 (2)0.046 (2)0.0036 (18)0.0143 (18)0.0081 (19)
C180.046 (2)0.049 (2)0.060 (3)0.0052 (19)0.021 (2)0.005 (2)
C190.103 (4)0.102 (4)0.057 (3)0.043 (3)0.025 (3)0.005 (3)
C200.145 (6)0.129 (5)0.063 (4)0.052 (5)0.041 (4)0.009 (3)
C210.103 (4)0.079 (4)0.093 (4)0.002 (3)0.063 (4)0.014 (3)
C220.089 (4)0.082 (4)0.101 (4)0.019 (3)0.054 (4)0.002 (3)
C230.077 (3)0.064 (3)0.074 (3)0.018 (3)0.029 (3)0.003 (2)
C240.040 (2)0.039 (2)0.061 (3)0.0035 (17)0.014 (2)0.0085 (18)
C250.054 (3)0.062 (3)0.065 (3)0.002 (2)0.017 (2)0.004 (2)
C260.086 (4)0.084 (4)0.082 (4)0.004 (3)0.045 (3)0.010 (3)
C270.080 (4)0.063 (3)0.142 (6)0.015 (3)0.063 (4)0.004 (4)
C280.056 (3)0.062 (3)0.129 (5)0.019 (2)0.034 (4)0.027 (3)
C290.053 (3)0.058 (3)0.072 (3)0.006 (2)0.019 (2)0.017 (2)
Geometric parameters (Å, º) top
Sn1—O22.074 (3)C12—C131.336 (6)
Sn1—C242.109 (4)C12—H120.9300
Sn1—C182.112 (4)C13—C141.411 (6)
Sn1—O12.117 (2)C13—H130.9300
Sn1—N32.141 (3)C14—C151.410 (6)
N1—C31.310 (6)C15—C161.344 (6)
N1—C41.329 (5)C15—H150.9300
N2—C61.297 (4)C16—C171.419 (5)
N2—N31.403 (4)C16—H160.9300
N3—C71.308 (4)C18—C191.355 (6)
O1—C61.307 (4)C18—C231.386 (6)
O2—C171.313 (4)C19—C201.380 (7)
C1—C51.369 (5)C19—H190.9300
C1—C21.380 (5)C20—C211.337 (7)
C1—C61.477 (5)C20—H200.9300
C2—C31.381 (6)C21—C221.347 (7)
C2—H20.9300C21—H210.9300
C3—H30.9300C22—C231.368 (6)
C4—C51.372 (5)C22—H220.9300
C4—H40.9300C23—H230.9300
C5—H50.9300C24—C291.375 (5)
C7—C81.419 (5)C24—C251.384 (6)
C7—H70.9300C25—C261.385 (6)
C8—C171.396 (5)C25—H250.9300
C8—C91.459 (5)C26—C271.355 (7)
C9—C101.399 (5)C26—H260.9300
C9—C141.414 (5)C27—C281.365 (7)
C10—C111.374 (5)C27—H270.9300
C10—H100.9300C28—C291.379 (7)
C11—C121.392 (6)C28—H280.9300
C11—H110.9300C29—H290.9300
O2—Sn1—C2496.74 (14)C11—C12—H12120.1
O2—Sn1—C1895.03 (14)C12—C13—C14121.7 (4)
C24—Sn1—C18120.33 (15)C12—C13—H13119.1
O2—Sn1—O1155.90 (10)C14—C13—H13119.1
C24—Sn1—O196.68 (13)C15—C14—C13121.5 (4)
C18—Sn1—O195.33 (14)C15—C14—C9119.2 (4)
O2—Sn1—N382.36 (10)C13—C14—C9119.3 (4)
C24—Sn1—N3112.95 (13)C16—C15—C14122.4 (4)
C18—Sn1—N3126.55 (13)C16—C15—H15118.8
O1—Sn1—N374.00 (10)C14—C15—H15118.8
C3—N1—C4115.7 (4)C15—C16—C17120.5 (4)
C6—N2—N3111.2 (3)C15—C16—H16119.8
C7—N3—N2115.3 (3)C17—C16—H16119.8
C7—N3—Sn1129.2 (2)O2—C17—C8124.1 (3)
N2—N3—Sn1115.5 (2)O2—C17—C16115.9 (3)
C6—O1—Sn1113.2 (2)C8—C17—C16120.0 (3)
C17—O2—Sn1133.6 (2)C19—C18—C23117.6 (4)
C5—C1—C2117.2 (3)C19—C18—Sn1122.8 (3)
C5—C1—C6122.9 (3)C23—C18—Sn1119.4 (3)
C2—C1—C6119.9 (4)C18—C19—C20120.5 (5)
C1—C2—C3118.8 (4)C18—C19—H19119.7
C1—C2—H2120.6C20—C19—H19119.7
C3—C2—H2120.6C21—C20—C19121.3 (5)
N1—C3—C2124.7 (5)C21—C20—H20119.4
N1—C3—H3117.7C19—C20—H20119.4
C2—C3—H3117.7C20—C21—C22119.2 (5)
N1—C4—C5124.3 (4)C20—C21—H21120.4
N1—C4—H4117.9C22—C21—H21120.4
C5—C4—H4117.9C21—C22—C23120.8 (5)
C1—C5—C4119.4 (4)C21—C22—H22119.6
C1—C5—H5120.3C23—C22—H22119.6
C4—C5—H5120.3C22—C23—C18120.6 (5)
N2—C6—O1124.9 (3)C22—C23—H23119.7
N2—C6—C1118.0 (3)C18—C23—H23119.7
O1—C6—C1117.1 (3)C29—C24—C25118.6 (4)
N3—C7—C8127.2 (3)C29—C24—Sn1120.6 (3)
N3—C7—H7116.4C25—C24—Sn1120.8 (3)
C8—C7—H7116.4C24—C25—C26120.1 (4)
C17—C8—C7122.1 (3)C24—C25—H25119.9
C17—C8—C9119.4 (3)C26—C25—H25119.9
C7—C8—C9118.5 (3)C27—C26—C25120.3 (5)
C10—C9—C14117.5 (4)C27—C26—H26119.8
C10—C9—C8124.0 (3)C25—C26—H26119.8
C14—C9—C8118.5 (4)C26—C27—C28120.1 (5)
C11—C10—C9121.4 (4)C26—C27—H27119.9
C11—C10—H10119.3C28—C27—H27119.9
C9—C10—H10119.3C27—C28—C29120.2 (5)
C10—C11—C12120.3 (5)C27—C28—H28119.9
C10—C11—H11119.8C29—C28—H28119.9
C12—C11—H11119.8C24—C29—C28120.5 (5)
C13—C12—C11119.8 (4)C24—C29—H29119.7
C13—C12—H12120.1C28—C29—H29119.7

Experimental details

Crystal data
Chemical formula[Sn(C6H5)2(C17H11N3O2)]
Mr562.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)10.283 (4), 21.060 (8), 11.984 (5)
β (°) 112.380 (5)
V3)2399.9 (15)
Z4
Radiation typeMo Kα
µ (mm1)1.10
Crystal size (mm)0.49 × 0.47 × 0.43
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.616, 0.650
No. of measured, independent and
observed [I > 2σ(I)] reflections
12415, 4205, 3087
Rint0.042
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.083, 1.03
No. of reflections4205
No. of parameters316
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.63, 0.48

Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected geometric parameters (Å, º) top
Sn1—O22.074 (3)Sn1—N32.141 (3)
Sn1—C242.109 (4)N2—C61.297 (4)
Sn1—C182.112 (4)N2—N31.403 (4)
Sn1—O12.117 (2)N3—C71.308 (4)
O2—Sn1—C2496.74 (14)C24—Sn1—C18120.33 (15)
O2—Sn1—C1895.03 (14)
 

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