[2-Oxido-1-naphthaldehyde oxido(4-pyrid­yl)methyl­hydrazone]diphenyl­tin(IV)

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)°.

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

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S1. Comment

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.

S2. Experimental

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%.

S3. Refinement

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

Computing details

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

	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.
	Fig. 2. The crystal packing of the title complex.

[2-Oxido-1-naphthaldehyde oxido(4-pyridyl)methylhydrazone]diphenyltin(IV)

Crystal data

[Sn(C6H5)2(C17H11N3O2)]	F(000) = 1128
Mr = 562.18	Dx = 1.556 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.283 (4) Å	Cell parameters from 4361 reflections
b = 21.060 (8) Å	θ = 2.4–24.7°
c = 11.984 (5) Å	µ = 1.10 mm^−1
β = 112.380 (5)°	T = 298 K
V = 2399.9 (15) Å^3	Block, orange
Z = 4	0.49 × 0.47 × 0.43 mm

Data collection

Siemens SMART CCD area-detector diffractometer	4205 independent reflections
Radiation source: fine-focus sealed tube	3087 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ϕ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.616, Tmax = 0.650	k = −25→23
12415 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0299P)^2 + 1.5741P] where P = (Fo^2 + 2Fc^2)/3
4205 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.51000 (3)	0.107422 (12)	0.72358 (2)	0.04583 (11)
N1	0.9571 (4)	−0.15598 (19)	0.9366 (4)	0.0785 (12)
N2	0.5352 (3)	−0.03155 (14)	0.6719 (3)	0.0462 (7)
N3	0.4402 (3)	0.01913 (13)	0.6316 (3)	0.0403 (7)
O1	0.6587 (3)	0.03852 (12)	0.8235 (2)	0.0582 (7)
O2	0.3226 (3)	0.13979 (12)	0.5944 (3)	0.0573 (7)
C1	0.7509 (4)	−0.06501 (18)	0.8241 (3)	0.0453 (9)
C2	0.8545 (5)	−0.0545 (2)	0.9364 (4)	0.0712 (13)
H2	0.8570	−0.0167	0.9774	0.085*
C3	0.9543 (6)	−0.1010 (3)	0.9868 (5)	0.0922 (18)
H3	1.0245	−0.0928	1.0618	0.111*
C4	0.8573 (5)	−0.1651 (2)	0.8280 (4)	0.0649 (12)
H4	0.8578	−0.2032	0.7889	0.078*
C5	0.7536 (4)	−0.12192 (18)	0.7698 (4)	0.0522 (10)
H5	0.6857	−0.1313	0.6942	0.063*
C6	0.6416 (4)	−0.01642 (17)	0.7690 (3)	0.0425 (9)
C7	0.3216 (4)	0.00568 (17)	0.5429 (3)	0.0427 (9)
H7	0.3118	−0.0356	0.5133	0.051*
C8	0.2062 (4)	0.04712 (17)	0.4868 (3)	0.0397 (8)
C9	0.0781 (4)	0.02110 (18)	0.3961 (3)	0.0443 (9)
C10	0.0618 (4)	−0.0425 (2)	0.3597 (4)	0.0564 (11)
H10	0.1361	−0.0706	0.3943	0.068*
C11	−0.0617 (5)	−0.0644 (2)	0.2738 (4)	0.0678 (12)
H11	−0.0705	−0.1071	0.2520	0.081*
C12	−0.1737 (5)	−0.0231 (3)	0.2194 (4)	0.0745 (14)
H12	−0.2564	−0.0378	0.1601	0.089*
C13	−0.1620 (4)	0.0379 (2)	0.2527 (4)	0.0678 (13)
H13	−0.2379	0.0650	0.2167	0.081*
C14	−0.0374 (4)	0.0622 (2)	0.3411 (3)	0.0506 (10)
C15	−0.0270 (4)	0.1261 (2)	0.3784 (4)	0.0582 (11)
H15	−0.1041	0.1527	0.3433	0.070*
C16	0.0905 (4)	0.15009 (19)	0.4627 (4)	0.0520 (10)
H16	0.0929	0.1924	0.4854	0.062*
C17	0.2109 (4)	0.11126 (17)	0.5174 (3)	0.0440 (9)
C18	0.4683 (4)	0.14178 (18)	0.8722 (4)	0.0513 (10)
C19	0.5447 (6)	0.1243 (3)	0.9875 (4)	0.0889 (17)
H19	0.6150	0.0939	1.0031	0.107*
C20	0.5189 (8)	0.1513 (3)	1.0820 (5)	0.112 (2)
H20	0.5718	0.1384	1.1606	0.134*
C21	0.4195 (6)	0.1956 (3)	1.0629 (5)	0.0838 (16)
H21	0.4049	0.2141	1.1276	0.101*
C22	0.3409 (6)	0.2129 (3)	0.9488 (5)	0.0854 (16)
H22	0.2700	0.2429	0.9348	0.102*
C23	0.3641 (5)	0.1870 (2)	0.8534 (4)	0.0717 (13)
H23	0.3094	0.1997	0.7753	0.086*
C24	0.6451 (4)	0.15789 (17)	0.6601 (4)	0.0482 (10)
C25	0.6111 (5)	0.1663 (2)	0.5376 (4)	0.0620 (11)
H25	0.5286	0.1489	0.4823	0.074*
C26	0.6994 (6)	0.2007 (2)	0.4973 (5)	0.0799 (14)
H26	0.6759	0.2063	0.4149	0.096*
C27	0.8198 (6)	0.2262 (2)	0.5772 (7)	0.0889 (17)
H27	0.8785	0.2494	0.5495	0.107*
C28	0.8552 (5)	0.2179 (2)	0.6981 (6)	0.0828 (16)
H28	0.9380	0.2353	0.7527	0.099*
C29	0.7684 (4)	0.1837 (2)	0.7397 (4)	0.0628 (12)
H29	0.7934	0.1780	0.8222	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03958 (17)	0.03933 (16)	0.05258 (18)	0.00157 (12)	0.01081 (12)	−0.00148 (13)
N1	0.070 (3)	0.077 (3)	0.072 (3)	0.035 (2)	0.008 (2)	0.003 (2)
N2	0.0391 (18)	0.0427 (18)	0.0487 (19)	0.0090 (14)	0.0077 (16)	0.0004 (15)
N3	0.0345 (17)	0.0385 (17)	0.0413 (17)	0.0035 (13)	0.0071 (14)	0.0015 (13)
O1	0.0529 (17)	0.0463 (16)	0.0551 (17)	0.0102 (13)	−0.0022 (14)	−0.0050 (13)
O2	0.0467 (17)	0.0389 (15)	0.0712 (19)	0.0027 (12)	0.0056 (15)	0.0018 (14)
C1	0.041 (2)	0.049 (2)	0.043 (2)	0.0060 (17)	0.0124 (18)	0.0042 (18)
C2	0.065 (3)	0.065 (3)	0.062 (3)	0.022 (2)	0.000 (2)	−0.009 (2)
C3	0.071 (3)	0.098 (4)	0.073 (3)	0.039 (3)	−0.013 (3)	−0.006 (3)
C4	0.065 (3)	0.057 (3)	0.071 (3)	0.018 (2)	0.025 (3)	0.000 (2)
C5	0.048 (2)	0.056 (3)	0.046 (2)	0.0096 (19)	0.010 (2)	0.0010 (19)
C6	0.042 (2)	0.040 (2)	0.044 (2)	0.0025 (16)	0.0141 (19)	0.0019 (17)
C7	0.041 (2)	0.041 (2)	0.044 (2)	0.0012 (16)	0.0132 (19)	0.0004 (17)
C8	0.034 (2)	0.045 (2)	0.037 (2)	0.0016 (16)	0.0108 (17)	0.0044 (17)
C9	0.039 (2)	0.055 (2)	0.038 (2)	0.0009 (18)	0.0145 (18)	0.0057 (18)
C10	0.044 (2)	0.062 (3)	0.054 (3)	−0.003 (2)	0.009 (2)	−0.003 (2)
C11	0.054 (3)	0.072 (3)	0.066 (3)	−0.008 (2)	0.009 (2)	−0.009 (2)
C12	0.050 (3)	0.097 (4)	0.061 (3)	−0.014 (3)	0.003 (2)	−0.002 (3)
C13	0.043 (3)	0.086 (4)	0.061 (3)	0.003 (2)	0.006 (2)	0.016 (3)
C14	0.039 (2)	0.063 (3)	0.046 (2)	0.0019 (19)	0.0120 (19)	0.013 (2)
C15	0.043 (2)	0.066 (3)	0.062 (3)	0.015 (2)	0.016 (2)	0.020 (2)
C16	0.043 (2)	0.048 (2)	0.060 (3)	0.0070 (18)	0.015 (2)	0.011 (2)
C17	0.037 (2)	0.048 (2)	0.046 (2)	0.0036 (18)	0.0143 (18)	0.0081 (19)
C18	0.046 (2)	0.049 (2)	0.060 (3)	−0.0052 (19)	0.021 (2)	−0.005 (2)
C19	0.103 (4)	0.102 (4)	0.057 (3)	0.043 (3)	0.025 (3)	0.005 (3)
C20	0.145 (6)	0.129 (5)	0.063 (4)	0.052 (5)	0.041 (4)	0.009 (3)
C21	0.103 (4)	0.079 (4)	0.093 (4)	−0.002 (3)	0.063 (4)	−0.014 (3)
C22	0.089 (4)	0.082 (4)	0.101 (4)	0.019 (3)	0.054 (4)	−0.002 (3)
C23	0.077 (3)	0.064 (3)	0.074 (3)	0.018 (3)	0.029 (3)	−0.003 (2)
C24	0.040 (2)	0.039 (2)	0.061 (3)	−0.0035 (17)	0.014 (2)	−0.0085 (18)
C25	0.054 (3)	0.062 (3)	0.065 (3)	−0.002 (2)	0.017 (2)	−0.004 (2)
C26	0.086 (4)	0.084 (4)	0.082 (4)	0.004 (3)	0.045 (3)	0.010 (3)
C27	0.080 (4)	0.063 (3)	0.142 (6)	−0.015 (3)	0.063 (4)	−0.004 (4)
C28	0.056 (3)	0.062 (3)	0.129 (5)	−0.019 (2)	0.034 (4)	−0.027 (3)
C29	0.053 (3)	0.058 (3)	0.072 (3)	−0.006 (2)	0.019 (2)	−0.017 (2)

Geometric parameters (Å, º)

Sn1—O2	2.074 (3)	C12—C13	1.336 (6)
Sn1—C24	2.109 (4)	C12—H12	0.9300
Sn1—C18	2.112 (4)	C13—C14	1.411 (6)
Sn1—O1	2.117 (2)	C13—H13	0.9300
Sn1—N3	2.141 (3)	C14—C15	1.410 (6)
N1—C3	1.310 (6)	C15—C16	1.344 (6)
N1—C4	1.329 (5)	C15—H15	0.9300
N2—C6	1.297 (4)	C16—C17	1.419 (5)
N2—N3	1.403 (4)	C16—H16	0.9300
N3—C7	1.308 (4)	C18—C19	1.355 (6)
O1—C6	1.307 (4)	C18—C23	1.386 (6)
O2—C17	1.313 (4)	C19—C20	1.380 (7)
C1—C5	1.369 (5)	C19—H19	0.9300
C1—C2	1.380 (5)	C20—C21	1.337 (7)
C1—C6	1.477 (5)	C20—H20	0.9300
C2—C3	1.381 (6)	C21—C22	1.347 (7)
C2—H2	0.9300	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.368 (6)
C4—C5	1.372 (5)	C22—H22	0.9300
C4—H4	0.9300	C23—H23	0.9300
C5—H5	0.9300	C24—C29	1.375 (5)
C7—C8	1.419 (5)	C24—C25	1.384 (6)
C7—H7	0.9300	C25—C26	1.385 (6)
C8—C17	1.396 (5)	C25—H25	0.9300
C8—C9	1.459 (5)	C26—C27	1.355 (7)
C9—C10	1.399 (5)	C26—H26	0.9300
C9—C14	1.414 (5)	C27—C28	1.365 (7)
C10—C11	1.374 (5)	C27—H27	0.9300
C10—H10	0.9300	C28—C29	1.379 (7)
C11—C12	1.392 (6)	C28—H28	0.9300
C11—H11	0.9300	C29—H29	0.9300
O2—Sn1—C24	96.74 (14)	C11—C12—H12	120.1
O2—Sn1—C18	95.03 (14)	C12—C13—C14	121.7 (4)
C24—Sn1—C18	120.33 (15)	C12—C13—H13	119.1
O2—Sn1—O1	155.90 (10)	C14—C13—H13	119.1
C24—Sn1—O1	96.68 (13)	C15—C14—C13	121.5 (4)
C18—Sn1—O1	95.33 (14)	C15—C14—C9	119.2 (4)
O2—Sn1—N3	82.36 (10)	C13—C14—C9	119.3 (4)
C24—Sn1—N3	112.95 (13)	C16—C15—C14	122.4 (4)
C18—Sn1—N3	126.55 (13)	C16—C15—H15	118.8
O1—Sn1—N3	74.00 (10)	C14—C15—H15	118.8
C3—N1—C4	115.7 (4)	C15—C16—C17	120.5 (4)
C6—N2—N3	111.2 (3)	C15—C16—H16	119.8
C7—N3—N2	115.3 (3)	C17—C16—H16	119.8
C7—N3—Sn1	129.2 (2)	O2—C17—C8	124.1 (3)
N2—N3—Sn1	115.5 (2)	O2—C17—C16	115.9 (3)
C6—O1—Sn1	113.2 (2)	C8—C17—C16	120.0 (3)
C17—O2—Sn1	133.6 (2)	C19—C18—C23	117.6 (4)
C5—C1—C2	117.2 (3)	C19—C18—Sn1	122.8 (3)
C5—C1—C6	122.9 (3)	C23—C18—Sn1	119.4 (3)
C2—C1—C6	119.9 (4)	C18—C19—C20	120.5 (5)
C1—C2—C3	118.8 (4)	C18—C19—H19	119.7
C1—C2—H2	120.6	C20—C19—H19	119.7
C3—C2—H2	120.6	C21—C20—C19	121.3 (5)
N1—C3—C2	124.7 (5)	C21—C20—H20	119.4
N1—C3—H3	117.7	C19—C20—H20	119.4
C2—C3—H3	117.7	C20—C21—C22	119.2 (5)
N1—C4—C5	124.3 (4)	C20—C21—H21	120.4
N1—C4—H4	117.9	C22—C21—H21	120.4
C5—C4—H4	117.9	C21—C22—C23	120.8 (5)
C1—C5—C4	119.4 (4)	C21—C22—H22	119.6
C1—C5—H5	120.3	C23—C22—H22	119.6
C4—C5—H5	120.3	C22—C23—C18	120.6 (5)
N2—C6—O1	124.9 (3)	C22—C23—H23	119.7
N2—C6—C1	118.0 (3)	C18—C23—H23	119.7
O1—C6—C1	117.1 (3)	C29—C24—C25	118.6 (4)
N3—C7—C8	127.2 (3)	C29—C24—Sn1	120.6 (3)
N3—C7—H7	116.4	C25—C24—Sn1	120.8 (3)
C8—C7—H7	116.4	C24—C25—C26	120.1 (4)
C17—C8—C7	122.1 (3)	C24—C25—H25	119.9
C17—C8—C9	119.4 (3)	C26—C25—H25	119.9
C7—C8—C9	118.5 (3)	C27—C26—C25	120.3 (5)
C10—C9—C14	117.5 (4)	C27—C26—H26	119.8
C10—C9—C8	124.0 (3)	C25—C26—H26	119.8
C14—C9—C8	118.5 (4)	C26—C27—C28	120.1 (5)
C11—C10—C9	121.4 (4)	C26—C27—H27	119.9
C11—C10—H10	119.3	C28—C27—H27	119.9
C9—C10—H10	119.3	C27—C28—C29	120.2 (5)
C10—C11—C12	120.3 (5)	C27—C28—H28	119.9
C10—C11—H11	119.8	C29—C28—H28	119.9
C12—C11—H11	119.8	C24—C29—C28	120.5 (5)
C13—C12—C11	119.8 (4)	C24—C29—H29	119.7
C13—C12—H12	120.1	C28—C29—H29	119.7