metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[2-Oxido-1-naphthaldehyde (2-hy­droxy­benzo­yl)hydrazonato]di­phenyl­tin(IV)

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: handongyin@163.com

(Received 5 October 2009; accepted 22 October 2009; online 28 October 2009)

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.

Related literature

For related structures, see: Chen et al. (2006[Chen, S.-W., Yin, H.-D. & Wang, D.-Q. (2006). Acta Cryst. E62, m28-m29.]); Yearwood et al. (2002[Yearwood, B., Parkin, S. & Atwood, D. A. (2002). Inorg. Chim. Acta, 333, 124-131.]). For covalent radii, see: Sanderson (1967[Sanderson, R. T. (1967). Inorganic Chemistry, p. 74. New York: Reinhold.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)2(C18H12N2O3)]

  • Mr = 577.19

  • Monoclinic, P 21 /c

  • a = 9.418 (1) Å

  • b = 11.0861 (12) Å

  • c = 25.668 (2) Å

  • β = 109.547 (2)°

  • V = 2525.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.05 mm−1

  • T = 293 K

  • 0.43 × 0.29 × 0.20 mm

Data collection
  • Siemens SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.662, Tmax = 0.818

  • 12414 measured reflections

  • 4435 independent reflections

  • 3263 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.073

  • S = 1.03

  • 4435 reflections

  • 325 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Selected bond lengths (Å)

Sn1—O1 2.121 (2)
Sn1—O3 2.061 (2)
Sn1—N2 2.154 (3)
Sn1—C19 2.106 (4)
Sn1—C25 2.113 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯N1 0.82 1.89 2.611 (5) 146

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

For related structures, see: Chen et al. (2006); Yearwood et al. (2002). For atomic covalent radii, see: Sanderson (1967).

Experimental top

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%.

Refinement top

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).

Structure description top

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.

For related structures, see: Chen et al. (2006); Yearwood et al. (2002). For atomic covalent radii, see: Sanderson (1967).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the title compound.
[2-Oxido-1-naphthaldehyde (2-hydroxybenzoyl)hydrazonato]diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C18H12N2O3)]F(000) = 1160
Mr = 577.19Dx = 1.518 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4435 reflections
a = 9.418 (1) Åθ = 2.5–24.5°
b = 11.0861 (12) ŵ = 1.05 mm1
c = 25.668 (2) ÅT = 293 K
β = 109.547 (2)°Block, colorless
V = 2525.5 (4) Å30.43 × 0.29 × 0.20 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD
diffractometer
4435 independent reflections
Radiation source: fine-focus sealed tube3263 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.662, Tmax = 0.818k = 1113
12414 measured reflectionsl = 3030
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) = 0.073H-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 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
[Sn(C6H5)2(C18H12N2O3)]V = 2525.5 (4) Å3
Mr = 577.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.418 (1) ŵ = 1.05 mm1
b = 11.0861 (12) ÅT = 293 K
c = 25.668 (2) Å0.43 × 0.29 × 0.20 mm
β = 109.547 (2)°
Data collection top
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 = 0.818Rint = 0.031
12414 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.073H-atom parameters constrained
S = 1.03Δρmax = 0.43 e Å3
4435 reflectionsΔρmin = 0.33 e Å3
325 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.89811 (3)0.74107 (2)0.920886 (10)0.04851 (10)
N10.8396 (4)0.4718 (2)0.91811 (11)0.0465 (8)
N20.8343 (3)0.5736 (2)0.94938 (11)0.0434 (7)
O10.9135 (3)0.6067 (2)0.86422 (10)0.0647 (8)
O20.7809 (4)0.2520 (2)0.88057 (12)0.0834 (10)
H20.78480.30890.90150.125*
O30.8815 (3)0.8048 (2)0.99407 (10)0.0589 (7)
C10.8817 (4)0.4984 (3)0.87560 (14)0.0459 (9)
C20.8935 (4)0.4009 (3)0.83892 (14)0.0493 (9)
C30.8422 (5)0.2849 (3)0.84222 (15)0.0576 (11)
C40.8529 (6)0.1978 (4)0.80504 (18)0.0794 (14)
H40.81930.11980.80750.095*
C50.9126 (7)0.2261 (5)0.7647 (2)0.0918 (17)
H50.91660.16760.73920.110*
C60.9665 (7)0.3391 (5)0.7614 (2)0.1001 (19)
H61.01000.35730.73470.120*
C70.9554 (6)0.4251 (4)0.79798 (17)0.0753 (14)
H70.99050.50250.79540.090*
C80.7840 (4)0.5562 (3)0.99031 (14)0.0449 (9)
H80.75500.47790.99500.054*
C90.7683 (4)0.6439 (3)1.02883 (13)0.0428 (9)
C100.8202 (4)0.7625 (3)1.02946 (14)0.0482 (9)
C110.8110 (5)0.8440 (3)1.07056 (15)0.0557 (10)
H110.84600.92251.07080.067*
C120.7523 (5)0.8097 (4)1.10938 (16)0.0609 (11)
H120.74960.86481.13640.073*
C130.6946 (5)0.6924 (4)1.11023 (16)0.0561 (11)
C140.7010 (4)0.6071 (3)1.07003 (15)0.0507 (10)
C150.6398 (5)0.4933 (4)1.07211 (17)0.0640 (12)
H150.64010.43631.04550.077*
C160.5797 (6)0.4627 (4)1.1119 (2)0.0826 (15)
H160.54100.38561.11220.099*
C170.5756 (6)0.5453 (5)1.1519 (2)0.0878 (16)
H170.53460.52421.17900.105*
C180.6327 (6)0.6582 (4)1.15106 (18)0.0751 (14)
H180.63080.71371.17800.090*
C191.1244 (4)0.7942 (3)0.93967 (14)0.0444 (9)
C201.2167 (5)0.8207 (3)0.99286 (15)0.0572 (11)
H201.17790.81791.02170.069*
C211.3657 (5)0.8514 (4)1.0035 (2)0.0748 (13)
H211.42750.86611.03960.090*
C221.4234 (6)0.8602 (4)0.9612 (2)0.0763 (13)
H221.52360.88210.96860.092*
C231.3339 (6)0.8371 (4)0.9084 (2)0.0707 (13)
H231.37230.84450.87960.085*
C241.1862 (5)0.8026 (3)0.89768 (16)0.0585 (11)
H241.12680.78460.86160.070*
C250.7141 (4)0.8331 (3)0.86445 (15)0.0508 (10)
C260.6817 (5)0.9491 (4)0.87485 (19)0.0700 (12)
H260.74120.98680.90710.084*
C270.5624 (6)1.0113 (5)0.8384 (2)0.0913 (16)
H270.54361.09070.84590.110*
C280.4723 (6)0.9565 (7)0.7916 (2)0.0969 (19)
H280.39110.99800.76740.116*
C290.5006 (6)0.8424 (7)0.7803 (2)0.0976 (18)
H290.43860.80500.74840.117*
C300.6228 (5)0.7797 (4)0.81640 (18)0.0751 (13)
H300.64270.70130.80790.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.05637 (18)0.04439 (15)0.04495 (15)0.01070 (14)0.01717 (12)0.00358 (12)
N10.058 (2)0.0411 (16)0.0412 (17)0.0028 (14)0.0175 (16)0.0055 (13)
N20.048 (2)0.0421 (16)0.0400 (17)0.0043 (14)0.0142 (15)0.0034 (13)
O10.094 (2)0.0545 (16)0.0572 (17)0.0219 (15)0.0407 (17)0.0132 (13)
O20.138 (3)0.0483 (16)0.079 (2)0.0149 (18)0.057 (2)0.0112 (15)
O30.080 (2)0.0532 (15)0.0504 (16)0.0166 (14)0.0309 (15)0.0128 (12)
C10.048 (3)0.046 (2)0.039 (2)0.0072 (18)0.0094 (18)0.0046 (16)
C20.054 (3)0.054 (2)0.036 (2)0.0022 (19)0.0113 (19)0.0059 (17)
C30.071 (3)0.053 (2)0.045 (2)0.008 (2)0.014 (2)0.0043 (18)
C40.114 (4)0.057 (3)0.067 (3)0.009 (3)0.029 (3)0.016 (2)
C50.120 (5)0.091 (4)0.065 (3)0.017 (3)0.032 (3)0.029 (3)
C60.142 (6)0.111 (4)0.064 (3)0.014 (4)0.056 (4)0.025 (3)
C70.097 (4)0.079 (3)0.057 (3)0.018 (3)0.037 (3)0.015 (2)
C80.051 (3)0.041 (2)0.044 (2)0.0003 (17)0.0162 (19)0.0026 (16)
C90.043 (2)0.045 (2)0.037 (2)0.0062 (17)0.0096 (17)0.0028 (15)
C100.047 (2)0.050 (2)0.044 (2)0.0035 (19)0.0112 (17)0.0021 (18)
C110.062 (3)0.050 (2)0.052 (2)0.002 (2)0.016 (2)0.0086 (18)
C120.068 (3)0.063 (3)0.053 (3)0.011 (2)0.021 (2)0.010 (2)
C130.060 (3)0.059 (2)0.052 (2)0.013 (2)0.023 (2)0.0021 (19)
C140.051 (3)0.052 (2)0.050 (2)0.0134 (19)0.018 (2)0.0057 (18)
C150.082 (4)0.058 (3)0.066 (3)0.005 (2)0.044 (3)0.003 (2)
C160.112 (5)0.071 (3)0.091 (4)0.001 (3)0.069 (3)0.007 (3)
C170.118 (5)0.089 (4)0.084 (4)0.014 (3)0.071 (4)0.014 (3)
C180.097 (4)0.077 (3)0.068 (3)0.016 (3)0.050 (3)0.003 (2)
C190.052 (2)0.0325 (18)0.047 (2)0.0046 (16)0.0141 (19)0.0030 (15)
C200.063 (3)0.062 (3)0.044 (2)0.007 (2)0.014 (2)0.0018 (18)
C210.059 (3)0.078 (3)0.068 (3)0.011 (3)0.004 (3)0.002 (2)
C220.055 (3)0.067 (3)0.106 (4)0.008 (2)0.027 (3)0.003 (3)
C230.076 (4)0.063 (3)0.089 (4)0.010 (2)0.048 (3)0.002 (2)
C240.067 (3)0.063 (2)0.047 (2)0.010 (2)0.022 (2)0.0004 (19)
C250.050 (3)0.056 (2)0.045 (2)0.0142 (19)0.0134 (19)0.0039 (17)
C260.059 (3)0.066 (3)0.077 (3)0.002 (2)0.012 (3)0.005 (2)
C270.080 (4)0.081 (4)0.106 (5)0.008 (3)0.021 (4)0.023 (3)
C280.058 (4)0.141 (6)0.088 (4)0.008 (4)0.019 (3)0.052 (4)
C290.070 (4)0.153 (6)0.055 (3)0.024 (4)0.001 (3)0.007 (4)
C300.076 (3)0.087 (3)0.054 (3)0.019 (3)0.011 (2)0.006 (2)
Geometric parameters (Å, º) top
Sn1—O12.121 (2)C13—C181.411 (5)
Sn1—O32.061 (2)C13—C141.415 (5)
Sn1—N22.154 (3)C14—C151.396 (5)
Sn1—C192.106 (4)C15—C161.366 (5)
Sn1—C252.113 (4)C15—H150.9300
N1—C11.313 (4)C16—C171.387 (6)
N1—N21.395 (4)C16—H160.9300
N2—C81.303 (4)C17—C181.365 (6)
O1—C11.294 (4)C17—H170.9300
O2—C31.348 (5)C18—H180.9300
O2—H20.8200C19—C201.383 (5)
O3—C101.315 (4)C19—C241.389 (5)
C1—C21.462 (5)C20—C211.380 (6)
C2—C31.386 (5)C20—H200.9300
C2—C71.388 (5)C21—C221.370 (6)
C3—C41.384 (5)C21—H210.9300
C4—C51.371 (6)C22—C231.359 (6)
C4—H40.9300C22—H220.9300
C5—C61.364 (7)C23—C241.378 (6)
C5—H50.9300C23—H230.9300
C6—C71.366 (6)C24—H240.9300
C6—H60.9300C25—C261.368 (5)
C7—H70.9300C25—C301.379 (5)
C8—C91.429 (5)C26—C271.382 (6)
C8—H80.9300C26—H260.9300
C9—C101.401 (5)C27—C281.360 (7)
C9—C141.461 (5)C27—H270.9300
C10—C111.414 (5)C28—C291.344 (8)
C11—C121.346 (5)C28—H280.9300
C11—H110.9300C29—C301.397 (7)
C12—C131.413 (6)C29—H290.9300
C12—H120.9300C30—H300.9300
O3—Sn1—C1994.31 (12)C18—C13—C14119.4 (4)
O3—Sn1—C2599.45 (13)C12—C13—C14119.6 (3)
C19—Sn1—C25123.88 (13)C15—C14—C13117.2 (3)
O3—Sn1—O1155.42 (10)C15—C14—C9124.3 (3)
C19—Sn1—O193.27 (12)C13—C14—C9118.4 (3)
C25—Sn1—O195.61 (13)C16—C15—C14122.2 (4)
O3—Sn1—N282.61 (10)C16—C15—H15118.9
C19—Sn1—N2122.65 (12)C14—C15—H15118.9
C25—Sn1—N2113.00 (13)C15—C16—C17120.7 (4)
O1—Sn1—N273.63 (10)C15—C16—H16119.6
C1—N1—N2112.1 (3)C17—C16—H16119.6
C8—N2—N1115.9 (3)C18—C17—C16119.0 (4)
C8—N2—Sn1128.2 (2)C18—C17—H17120.5
N1—N2—Sn1115.7 (2)C16—C17—H17120.5
C1—O1—Sn1115.0 (2)C17—C18—C13121.4 (4)
C3—O2—H2109.5C17—C18—H18119.3
C10—O3—Sn1133.8 (2)C13—C18—H18119.3
O1—C1—N1123.6 (3)C20—C19—C24117.7 (4)
O1—C1—C2117.9 (3)C20—C19—Sn1122.6 (3)
N1—C1—C2118.6 (3)C24—C19—Sn1119.7 (3)
C3—C2—C7118.0 (3)C21—C20—C19120.6 (4)
C3—C2—C1122.9 (3)C21—C20—H20119.7
C7—C2—C1119.1 (4)C19—C20—H20119.7
O2—C3—C4117.6 (4)C22—C21—C20120.5 (4)
O2—C3—C2122.6 (3)C22—C21—H21119.8
C4—C3—C2119.9 (4)C20—C21—H21119.8
C5—C4—C3120.2 (5)C23—C22—C21119.9 (5)
C5—C4—H4119.9C23—C22—H22120.1
C3—C4—H4119.9C21—C22—H22120.1
C6—C5—C4120.8 (4)C22—C23—C24120.0 (4)
C6—C5—H5119.6C22—C23—H23120.0
C4—C5—H5119.6C24—C23—H23120.0
C5—C6—C7118.9 (5)C23—C24—C19121.3 (4)
C5—C6—H6120.5C23—C24—H24119.3
C7—C6—H6120.5C19—C24—H24119.3
C6—C7—C2122.2 (5)C26—C25—C30117.7 (4)
C6—C7—H7118.9C26—C25—Sn1120.3 (3)
C2—C7—H7118.9C30—C25—Sn1121.9 (3)
N2—C8—C9127.4 (3)C25—C26—C27121.4 (5)
N2—C8—H8116.3C25—C26—H26119.3
C9—C8—H8116.3C27—C26—H26119.3
C10—C9—C8122.0 (3)C28—C27—C26120.0 (5)
C10—C9—C14119.2 (3)C28—C27—H27120.0
C8—C9—C14118.8 (3)C26—C27—H27120.0
O3—C10—C9124.0 (3)C29—C28—C27120.1 (5)
O3—C10—C11115.9 (3)C29—C28—H28120.0
C9—C10—C11120.0 (3)C27—C28—H28120.0
C12—C11—C10121.0 (4)C28—C29—C30120.3 (5)
C12—C11—H11119.5C28—C29—H29119.9
C10—C11—H11119.5C30—C29—H29119.9
C11—C12—C13121.8 (4)C25—C30—C29120.5 (5)
C11—C12—H12119.1C25—C30—H30119.7
C13—C12—H12119.1C29—C30—H30119.7
C18—C13—C12121.0 (4)
C1—N1—N2—C8175.7 (3)C11—C12—C13—C18179.6 (4)
C1—N1—N2—Sn10.9 (4)C11—C12—C13—C141.3 (6)
O3—Sn1—N2—C811.5 (3)C18—C13—C14—C152.1 (6)
C19—Sn1—N2—C8101.9 (3)C12—C13—C14—C15178.8 (4)
C25—Sn1—N2—C885.7 (3)C18—C13—C14—C9178.8 (4)
O1—Sn1—N2—C8174.9 (3)C12—C13—C14—C90.3 (6)
O3—Sn1—N2—N1172.4 (2)C10—C9—C14—C15177.3 (4)
C19—Sn1—N2—N182.1 (3)C8—C9—C14—C154.9 (6)
C25—Sn1—N2—N190.4 (3)C10—C9—C14—C131.8 (5)
O1—Sn1—N2—N11.2 (2)C8—C9—C14—C13176.0 (3)
O3—Sn1—O1—C114.0 (5)C13—C14—C15—C161.8 (7)
C19—Sn1—O1—C1121.8 (3)C9—C14—C15—C16179.2 (4)
C25—Sn1—O1—C1113.7 (3)C14—C15—C16—C170.7 (8)
N2—Sn1—O1—C11.3 (3)C15—C16—C17—C180.0 (8)
C19—Sn1—O3—C10137.9 (3)C16—C17—C18—C130.4 (8)
C25—Sn1—O3—C1096.7 (3)C12—C13—C18—C17179.4 (5)
O1—Sn1—O3—C1030.3 (5)C14—C13—C18—C171.5 (7)
N2—Sn1—O3—C1015.5 (3)O3—Sn1—C19—C2017.9 (3)
Sn1—O1—C1—N11.4 (5)C25—Sn1—C19—C20122.4 (3)
Sn1—O1—C1—C2178.6 (3)O1—Sn1—C19—C20138.7 (3)
N2—N1—C1—O10.3 (5)N2—Sn1—C19—C2066.0 (3)
N2—N1—C1—C2179.7 (3)O3—Sn1—C19—C24162.6 (3)
O1—C1—C2—C3170.6 (4)C25—Sn1—C19—C2458.2 (3)
N1—C1—C2—C39.4 (6)O1—Sn1—C19—C2440.8 (3)
O1—C1—C2—C77.9 (6)N2—Sn1—C19—C24113.5 (3)
N1—C1—C2—C7172.1 (4)C24—C19—C20—C211.6 (6)
C7—C2—C3—O2179.7 (4)Sn1—C19—C20—C21177.9 (3)
C1—C2—C3—O21.8 (6)C19—C20—C21—C222.3 (7)
C7—C2—C3—C40.5 (6)C20—C21—C22—C230.9 (7)
C1—C2—C3—C4178.0 (4)C21—C22—C23—C241.2 (7)
O2—C3—C4—C5179.3 (5)C22—C23—C24—C191.9 (7)
C2—C3—C4—C50.6 (7)C20—C19—C24—C230.5 (6)
C3—C4—C5—C61.9 (8)Sn1—C19—C24—C23180.0 (3)
C4—C5—C6—C72.1 (9)O3—Sn1—C25—C2637.8 (3)
C5—C6—C7—C21.1 (9)C19—Sn1—C25—C2664.0 (4)
C3—C2—C7—C60.2 (7)O1—Sn1—C25—C26161.7 (3)
C1—C2—C7—C6178.4 (5)N2—Sn1—C25—C26123.7 (3)
N1—N2—C8—C9179.4 (3)O3—Sn1—C25—C30142.1 (3)
Sn1—N2—C8—C94.6 (6)C19—Sn1—C25—C30116.1 (3)
N2—C8—C9—C105.8 (6)O1—Sn1—C25—C3018.4 (3)
N2—C8—C9—C14176.5 (4)N2—Sn1—C25—C3056.2 (4)
Sn1—O3—C10—C911.6 (6)C30—C25—C26—C270.4 (7)
Sn1—O3—C10—C11169.6 (3)Sn1—C25—C26—C27179.7 (4)
C8—C9—C10—O32.8 (6)C25—C26—C27—C281.4 (8)
C14—C9—C10—O3179.5 (3)C26—C27—C28—C291.0 (8)
C8—C9—C10—C11176.0 (3)C27—C28—C29—C300.3 (8)
C14—C9—C10—C111.7 (5)C26—C25—C30—C290.9 (7)
O3—C10—C11—C12179.0 (4)Sn1—C25—C30—C29179.0 (4)
C9—C10—C11—C120.2 (6)C28—C29—C30—C251.2 (8)
C10—C11—C12—C131.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.892.611 (5)146

Experimental details

Crystal data
Chemical formula[Sn(C6H5)2(C18H12N2O3)]
Mr577.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.418 (1), 11.0861 (12), 25.668 (2)
β (°) 109.547 (2)
V3)2525.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.05
Crystal size (mm)0.43 × 0.29 × 0.20
Data collection
DiffractometerSiemens SMART 1000 CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.662, 0.818
No. of measured, independent and
observed [I > 2σ(I)] reflections
12414, 4435, 3263
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.073, 1.03
No. of reflections4435
No. of parameters325
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.33

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Sn1—O12.121 (2)Sn1—C192.106 (4)
Sn1—O32.061 (2)Sn1—C252.113 (4)
Sn1—N22.154 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.892.611 (5)146
 

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

References

First citationChen, S.-W., Yin, H.-D. & Wang, D.-Q. (2006). Acta Cryst. E62, m28–m29.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSanderson, R. T. (1967). Inorganic Chemistry, p. 74. New York: Reinhold.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationYearwood, B., Parkin, S. & Atwood, D. A. (2002). Inorg. Chim. Acta, 333, 124–131.  Web of Science CSD CrossRef CAS Google Scholar

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