Bis(μ-2-{[oxido(phenyl)methylidene]hydrazinylidene}propanoato)bis[dibenzyl(ethanol)tin(IV)]

Sun, S.; Yang, J.

doi:10.1107/S1600536811011937

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m544

doi:10.1107/S1600536811011937

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Bis(μ-2-{[oxido(phenyl)methylidene]hydrazinylidene}propanoato)bis[dibenzyl(ethanol)tin(IV)]

Shaojun Sun ^a ^* and Jie Yang ^b

^aClinical Laboratory, Liaocheng Hospital, Liaocheng 252000, People's Republic of China, and ^bChinese Medicine Hospital of Liaocheng, Liaocheng 252000, People's Republic of China
^*Correspondence e-mail: shenghuashi6@126.com

(Received 2 March 2011; accepted 31 March 2011; online 7 April 2011)

In the title complex, [Sn₂(C₇H₇)₄(C₁₀H₈N₂O₃)₂(C₂H₅OH)₂], the Sn(IV) atom is seven-coordinated in a distorted pentagonal–bipyramidal geometry by three O atoms and one N atom from the pyruvate benzoyl hydrazone ligand, one ethanol O atom and two axial C atoms from trans-benzyl groups, thus forming a dimeric molecule ( $[\overline{1}]$ symmetry) via weak Sn—O interactions. The C atoms of one phenyl ring and the ethanol molecule are disordered over two sets of sites with site-occupancy factors of 0.57 (5):0.43 (5) and 0.79 (2):0.21 (2), respectively. Intermolecular O—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For related structures, see: Sun & Hu (2007 ); Gielen et al. (2002 ).

Experimental

Crystal data

[Sn₂(C₇H₇)₄(C₁₀H₈N₂O₃)₂(C₂H₆O)₂]
M_r = 1102.42
Triclinic, $[P \overline 1]$
a = 8.7187 (18) Å
b = 11.385 (2) Å
c = 13.198 (3) Å
α = 96.170 (3)°
β = 93.728 (2)°
γ = 105.861 (3)°
V = 1246.8 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 298 K
0.45 × 0.37 × 0.23 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.647, T_max = 0.793
6566 measured reflections
4356 independent reflections
3598 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.08
4356 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 1.04 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C11	2.135 (6)
Sn1—O3	2.148 (3)
Sn1—C18	2.154 (6)
Sn1—N1	2.237 (4)
Sn1—O1	2.341 (3)
Sn1—O4	2.382 (4)
Sn1—O1ⁱ	2.772 (3)

C11—Sn1—O3	97.42 (19)
C11—Sn1—C18	163.3 (2)
O3—Sn1—C18	94.77 (18)
C11—Sn1—N1	97.9 (2)
O3—Sn1—N1	70.83 (13)
C18—Sn1—N1	96.85 (18)
C11—Sn1—O1	88.59 (19)
O3—Sn1—O1	140.42 (12)
C18—Sn1—O1	89.30 (18)
N1—Sn1—O1	69.60 (12)
C11—Sn1—O4	84.9 (2)
O3—Sn1—O4	78.79 (13)
C18—Sn1—O4	86.28 (19)
N1—Sn1—O4	149.60 (14)
O1—Sn1—O4	140.79 (12)
C11—Sn1—O1ⁱ	80.32 (18)
O3—Sn1—O1ⁱ	154.13 (12)
C18—Sn1—O1ⁱ	83.72 (16)
N1—Sn1—O1ⁱ	135.04 (12)
O1—Sn1—O1ⁱ	65.45 (12)
O4—Sn1—O1ⁱ	75.34 (11)
Symmetry code: (i) -x+2, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2ⁱ	0.82	1.82	2.624 (6)	165
Symmetry code: (i) -x+2, -y+2, -z.

Data collection: SMART (Siemens, 1996 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011937/lr2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011937/lr2004Isup2.hkl

checkCIF report

Comment top

Organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen et al., 2002). In our ongoing studies with Schiff base organotin(IV) compounds, the title compound has been synthesized and we report herein its crystal structure. The molecular structure of the compound is shown in Fig.1. The atoms O1, O3, N1 and O4 are coplanar within 0.0120 Å, which form the equatorial plane. Furthermore, the angle of the axial C11—Sn1—C18 is 163.3 (3)°, which deviates from the linear angle of 180°. These data indicate that the tin atom of this complex is in a distorted octahedral configuration. The O1 atom of the carboxylate residue also binds the other tin atom, Snⁱ, generating a Sn₂O₂ four-membered ring [symmetry code: 2 - x, 2 - y, -z]. The distances of Sn1–O1ⁱ 2.772 (4)Å are relatively longer than those of Sn1—O1 2.339 (4)Å (Table 1), but are comparable with those found in related seven-coordinate diorganotin systems (Sun et al., 2007). With weak interactions of Sn–O bonding, the structure of the title complex can be described as a dimer with crystallographically imposed 1 symmetry. and the coordination geometry of tin can be also described as a trans-C₂SnO₄N pentagonal bipyramid with the two benzyl groups occupying trans positions. The forming of the dimer leads to the shorter interaction between O and Oⁱ, because the interaction of two monomers surpass the repelling effect of two O atoms. Otherwise, there exhibit the disorder at the C12 to C17 aromatic ring moiety and the C25, C26 atoms of the coordinated ethonal solvate molecule.

Each Sn atom is also coordinated by an ethanol molecule, the Sn1—O4 bond distance being 2.424 (3) Å, which is comparable with those in the analogous (Sun et al., 2007), due to the formation of intradimeric hydrogen bonds, O2–O4ⁱ (or O2ⁱ–O4) 2.624 (6)Å (Table 2). These hydrogen bonds contribute to the stability and compactness of the crystal structure (Fig. 2).

Related literature top

For related structures, see: Sun & Hu (2007); Gielen et al. (2002).

Experimental top

Pyruvic acid benzoyldrazone (1 mmol) and sodium ethoxide (1 mmol) was added to the solution of dry benzene (20 ml) in a Schlenk flask and stirred for 0.5 h. Dibenzyltin dichloride (1 mmol) was then added and the reaction mixture was stirred for 12 h at 313 K and then filtered. The solvent was gradually removed by evaporation under vacuum until a solid product was obtained. The solid was then recrystallized from ethanol and colorless crystals suitable for X-ray diffraction were obtained. Elemental analysis, calculated for C₂₆H₂₈N₂O₄Sn: C 56.66, H 5.12, N 5.08; found: C 56.51, H 5.34, N 5.01%.

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

	Fig. 1. The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. Symmetry code: 2 - x, 2 - y, -z.
	Fig. 2. The crystal packing in a unit cell of the title complex, viewed along the b axis. H atoms have been omitted.

Bis(µ-2-{[oxido(phenyl)methylidene]hydrazinylidene}propanoato) bis[dibenzyl(ethanol)tin(IV)] top

Crystal data top

[Sn₂(C₇H₇)₄(C₁₀H₈N₂O₃)₂(C₂H₆O)₂]	Z = 1
M_r = 1102.42	F(000) = 560
Triclinic, P1	D_x = 1.468 Mg m⁻³
a = 8.7187 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.385 (2) Å	Cell parameters from 3583 reflections
c = 13.198 (3) Å	θ = 2.6–27.3°
α = 96.170 (3)°	µ = 1.06 mm⁻¹
β = 93.728 (2)°	T = 298 K
γ = 105.861 (3)°	Block, colorless
V = 1246.8 (4) Å³	0.45 × 0.37 × 0.23 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	4356 independent reflections
Radiation source: fine-focus sealed tube	3598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
phi and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.647, T_max = 0.793	k = −13→12
6566 measured reflections	l = −15→15

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0509P)² + 2.1936P] where P = (F_o² + 2F_c²)/3
4356 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 1.04 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Sn₂(C₇H₇)₄(C₁₀H₈N₂O₃)₂(C₂H₆O)₂]	γ = 105.861 (3)°
M_r = 1102.42	V = 1246.8 (4) Å³
Triclinic, P1	Z = 1
a = 8.7187 (18) Å	Mo Kα radiation
b = 11.385 (2) Å	µ = 1.06 mm⁻¹
c = 13.198 (3) Å	T = 298 K
α = 96.170 (3)°	0.45 × 0.37 × 0.23 mm
β = 93.728 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4356 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3598 reflections with I > 2σ(I)
T_min = 0.647, T_max = 0.793	R_int = 0.017
6566 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.08	Δρ_max = 1.04 e Å⁻³
4356 reflections	Δρ_min = −0.58 e Å⁻³
298 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.93329 (4)	0.91659 (3)	0.13554 (2)	0.04906 (15)
N1	0.7188 (5)	0.9747 (4)	0.1792 (3)	0.0470 (9)
N2	0.6493 (5)	0.9324 (4)	0.2637 (3)	0.0512 (10)
O1	0.8691 (4)	1.0434 (3)	0.0211 (2)	0.0504 (8)
O2	0.7086 (5)	1.1605 (4)	−0.0098 (3)	0.0724 (12)
O3	0.8542 (4)	0.8390 (3)	0.2709 (2)	0.0538 (9)
O4	1.1210 (5)	0.8036 (4)	0.1661 (3)	0.0688 (11)
H4	1.1866	0.8112	0.1237	0.103*
C1	0.7536 (6)	1.0884 (5)	0.0400 (4)	0.0509 (12)
C2	0.6661 (6)	1.0494 (5)	0.1312 (4)	0.0506 (12)
C3	0.5333 (7)	1.0990 (6)	0.1618 (4)	0.0679 (16)
H3A	0.4925	1.0645	0.2212	0.102*
H3B	0.4492	1.0778	0.1066	0.102*
H3C	0.5720	1.1870	0.1774	0.102*
C4	0.7284 (6)	0.8633 (5)	0.3039 (4)	0.0537 (12)
C5	0.6677 (6)	0.8078 (5)	0.3953 (4)	0.0569 (13)
C6	0.5814 (8)	0.8628 (6)	0.4586 (4)	0.0730 (17)
H6	0.5608	0.9355	0.4441	0.088*
C7	0.5253 (9)	0.8109 (7)	0.5433 (5)	0.0824 (19)
H7	0.4656	0.8484	0.5851	0.099*
C8	0.5554 (9)	0.7072 (7)	0.5662 (5)	0.086 (2)
H8	0.5173	0.6736	0.6240	0.104*
C9	0.6420 (8)	0.6504 (7)	0.5052 (5)	0.0817 (19)
H9	0.6628	0.5783	0.5210	0.098*
C10	0.6986 (8)	0.7022 (6)	0.4190 (4)	0.0717 (16)
H10	0.7580	0.6644	0.3772	0.086*
C11	0.8119 (8)	0.7607 (5)	0.0268 (4)	0.0695 (16)
H11A	0.7330	0.7837	−0.0161	0.083*
H11B	0.8892	0.7414	−0.0170	0.083*
C12	0.73 (9)	0.65 (8)	0.07 (6)	0.08 (4)	0.57 (5)
C13	0.804 (3)	0.5516 (19)	0.065 (3)	0.084 (6)	0.57 (5)
H13	0.8992	0.5572	0.0352	0.100*	0.57 (5)
C14	0.723 (3)	0.4437 (19)	0.110 (2)	0.087 (6)	0.57 (5)
H14	0.7650	0.3766	0.1083	0.105*	0.57 (5)
C15	0.582 (4)	0.440 (4)	0.156 (2)	0.090 (9)	0.57 (5)
H15	0.5369	0.3732	0.1897	0.108*	0.57 (5)
C16	0.504 (4)	0.533 (3)	0.1544 (19)	0.087 (8)	0.57 (5)
H16	0.4062	0.5260	0.1805	0.105*	0.57 (5)
C17	0.584 (7)	0.638 (5)	0.110 (3)	0.080 (8)	0.57 (5)
H17	0.5378	0.7020	0.1088	0.096*	0.57 (5)
C12'	0.71 (12)	0.66 (11)	0.08 (7)	0.08 (5)	0.43 (5)
C13'	0.771 (4)	0.562 (3)	0.116 (3)	0.085 (8)	0.43 (5)
H13'	0.8775	0.5638	0.1114	0.101*	0.43 (5)
C14'	0.668 (5)	0.466 (4)	0.159 (4)	0.087 (12)	0.43 (5)
H14'	0.7032	0.4010	0.1792	0.105*	0.43 (5)
C15'	0.510 (7)	0.472 (3)	0.172 (3)	0.085 (10)	0.43 (5)
H15'	0.4456	0.4140	0.2079	0.102*	0.43 (5)
C16'	0.447 (5)	0.562 (4)	0.133 (3)	0.087 (9)	0.43 (5)
H16'	0.3407	0.5608	0.1378	0.105*	0.43 (5)
C17'	0.551 (9)	0.654 (6)	0.086 (4)	0.080 (10)	0.43 (5)
H17'	0.5130	0.7144	0.0590	0.096*	0.43 (5)
C18	1.1115 (7)	1.0740 (5)	0.2175 (4)	0.0601 (14)
H18A	1.1875	1.0456	0.2581	0.072*
H18B	1.1696	1.1219	0.1684	0.072*
C19	1.0435 (7)	1.1550 (6)	0.2859 (4)	0.0598 (14)
C20	1.0187 (8)	1.2612 (6)	0.2555 (5)	0.0770 (17)
H20	1.0463	1.2836	0.1919	0.092*
C21	0.9518 (9)	1.3352 (7)	0.3206 (6)	0.092 (2)
H21	0.9346	1.4069	0.3007	0.110*
C22	0.9123 (9)	1.3008 (8)	0.4137 (6)	0.094 (2)
H22	0.8676	1.3497	0.4569	0.113*
C23	0.9365 (9)	1.1978 (8)	0.4443 (5)	0.088 (2)
H23	0.9088	1.1763	0.5081	0.105*
C24	1.0019 (8)	1.1246 (6)	0.3818 (4)	0.0721 (16)
H24	1.0187	1.0537	0.4036	0.086*
C25	1.2109 (15)	0.7949 (13)	0.2607 (7)	0.075 (3)	0.79 (2)
H25A	1.1945	0.8530	0.3153	0.090*	0.79 (2)
H25B	1.3244	0.8163	0.2518	0.090*	0.79 (2)
C26	1.1585 (19)	0.6675 (12)	0.2895 (11)	0.110 (5)	0.79 (2)
H26A	1.0507	0.6509	0.3080	0.165*	0.79 (2)
H26B	1.2283	0.6609	0.3466	0.165*	0.79 (2)
H26C	1.1629	0.6091	0.2324	0.165*	0.79 (2)
C25'	1.120 (7)	0.719 (5)	0.238 (3)	0.082 (12)	0.21 (2)
H25C	1.0292	0.6468	0.2190	0.099*	0.21 (2)
H25D	1.1083	0.7569	0.3053	0.099*	0.21 (2)
C26'	1.274 (7)	0.681 (4)	0.241 (4)	0.110 (18)	0.21 (2)
H26D	1.2485	0.5930	0.2267	0.165*	0.21 (2)
H26E	1.3307	0.7075	0.3082	0.165*	0.21 (2)
H26F	1.3391	0.7184	0.1911	0.165*	0.21 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0480 (2)	0.0633 (3)	0.0411 (2)	0.02061 (17)	0.01282 (14)	0.01142 (15)
N1	0.040 (2)	0.063 (3)	0.039 (2)	0.0126 (19)	0.0118 (17)	0.0094 (19)
N2	0.042 (2)	0.069 (3)	0.042 (2)	0.012 (2)	0.0105 (18)	0.010 (2)
O1	0.0480 (19)	0.069 (2)	0.0437 (18)	0.0262 (17)	0.0145 (15)	0.0146 (16)
O2	0.086 (3)	0.099 (3)	0.061 (2)	0.058 (3)	0.033 (2)	0.037 (2)
O3	0.052 (2)	0.068 (2)	0.0473 (19)	0.0206 (18)	0.0159 (16)	0.0149 (17)
O4	0.070 (3)	0.096 (3)	0.059 (2)	0.042 (2)	0.0245 (19)	0.030 (2)
C1	0.050 (3)	0.063 (3)	0.045 (3)	0.025 (3)	0.008 (2)	0.008 (2)
C2	0.047 (3)	0.065 (3)	0.044 (3)	0.020 (2)	0.011 (2)	0.010 (2)
C3	0.062 (4)	0.093 (4)	0.062 (3)	0.037 (3)	0.023 (3)	0.018 (3)
C4	0.057 (3)	0.064 (3)	0.041 (3)	0.016 (3)	0.011 (2)	0.011 (2)
C5	0.051 (3)	0.075 (4)	0.044 (3)	0.011 (3)	0.012 (2)	0.016 (3)
C6	0.076 (4)	0.094 (5)	0.052 (3)	0.021 (4)	0.023 (3)	0.020 (3)
C7	0.083 (5)	0.105 (5)	0.058 (4)	0.017 (4)	0.027 (3)	0.019 (4)
C8	0.085 (5)	0.106 (6)	0.061 (4)	0.003 (4)	0.021 (3)	0.029 (4)
C9	0.083 (5)	0.085 (5)	0.073 (4)	0.007 (4)	0.017 (4)	0.030 (4)
C10	0.073 (4)	0.084 (4)	0.058 (3)	0.017 (3)	0.015 (3)	0.018 (3)
C11	0.082 (4)	0.070 (4)	0.054 (3)	0.018 (3)	0.009 (3)	0.004 (3)
C12	0.09 (11)	0.07 (8)	0.06 (9)	0.02 (6)	0.00 (5)	0.01 (6)
C13	0.099 (12)	0.076 (10)	0.074 (14)	0.024 (8)	−0.004 (10)	0.010 (10)
C14	0.103 (13)	0.078 (11)	0.075 (14)	0.018 (9)	−0.004 (10)	0.011 (9)
C15	0.10 (3)	0.083 (19)	0.077 (12)	0.013 (17)	−0.002 (17)	0.016 (12)
C16	0.103 (19)	0.079 (19)	0.073 (14)	0.015 (16)	−0.002 (11)	0.015 (12)
C17	0.09 (2)	0.075 (16)	0.066 (19)	0.014 (13)	0.001 (14)	0.011 (12)
C12'	0.09 (16)	0.07 (10)	0.06 (12)	0.02 (8)	0.00 (8)	0.01 (8)
C13'	0.098 (16)	0.079 (14)	0.072 (17)	0.018 (11)	−0.004 (13)	0.015 (14)
C14'	0.10 (3)	0.08 (2)	0.074 (19)	0.011 (18)	0.00 (2)	0.018 (15)
C15'	0.10 (3)	0.08 (2)	0.074 (15)	0.020 (19)	−0.003 (15)	0.017 (15)
C16'	0.10 (2)	0.081 (18)	0.073 (16)	0.014 (14)	−0.001 (14)	0.012 (12)
C17'	0.09 (3)	0.075 (19)	0.07 (3)	0.014 (15)	0.001 (19)	0.011 (15)
C18	0.053 (3)	0.076 (4)	0.053 (3)	0.020 (3)	0.008 (2)	0.009 (3)
C19	0.052 (3)	0.072 (4)	0.051 (3)	0.013 (3)	0.004 (2)	0.004 (3)
C20	0.075 (4)	0.084 (5)	0.070 (4)	0.023 (4)	0.004 (3)	0.000 (3)
C21	0.089 (5)	0.090 (5)	0.093 (5)	0.027 (4)	−0.001 (4)	−0.004 (4)
C22	0.084 (5)	0.104 (6)	0.087 (5)	0.023 (4)	0.015 (4)	−0.021 (5)
C23	0.080 (5)	0.100 (6)	0.070 (4)	0.010 (4)	0.017 (4)	−0.009 (4)
C24	0.069 (4)	0.082 (4)	0.058 (3)	0.012 (3)	0.011 (3)	0.001 (3)
C25	0.073 (7)	0.090 (8)	0.069 (6)	0.026 (6)	0.015 (5)	0.025 (5)
C26	0.127 (11)	0.117 (9)	0.099 (9)	0.049 (8)	0.005 (8)	0.033 (7)
C25'	0.09 (3)	0.08 (3)	0.07 (2)	0.03 (3)	0.00 (2)	0.02 (2)
C26'	0.13 (4)	0.12 (3)	0.10 (3)	0.05 (3)	0.01 (3)	0.03 (2)

Geometric parameters (Å, º) top

Sn1—C11	2.135 (6)	C15—C16	1.40 (4)
Sn1—O3	2.148 (3)	C15—H15	0.9300
Sn1—C18	2.154 (6)	C16—C17	1.41 (6)
Sn1—N1	2.237 (4)	C16—H16	0.9300
Sn1—O1	2.341 (3)	C17—H17	0.9300
Sn1—O4	2.382 (4)	C12'—C13'	1.4 (12)
Sn1—O1ⁱ	2.772 (3)	C12'—C17'	1.4 (9)
N1—C2	1.276 (6)	C13'—C14'	1.41 (4)
N1—N2	1.373 (5)	C13'—H13'	0.9300
N2—C4	1.310 (7)	C14'—C15'	1.41 (6)
O1—C1	1.276 (6)	C14'—H14'	0.9300
O2—C1	1.233 (6)	C15'—C16'	1.42 (4)
O3—C4	1.293 (6)	C15'—H15'	0.9300
O4—C25'	1.42 (4)	C16'—C17'	1.42 (9)
O4—C25	1.458 (10)	C16'—H16'	0.9300
O4—H4	0.8200	C17'—H17'	0.9300
C1—C2	1.508 (7)	C18—C19	1.485 (8)
C2—C3	1.481 (7)	C18—H18A	0.9700
C3—H3A	0.9600	C18—H18B	0.9700
C3—H3B	0.9600	C19—C20	1.380 (9)
C3—H3C	0.9600	C19—C24	1.392 (8)
C4—C5	1.483 (7)	C20—C21	1.403 (9)
C5—C10	1.364 (8)	C20—H20	0.9300
C5—C6	1.372 (8)	C21—C22	1.366 (10)
C6—C7	1.376 (8)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.345 (11)
C7—C8	1.338 (10)	C22—H22	0.9300
C7—H7	0.9300	C23—C24	1.369 (9)
C8—C9	1.368 (10)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.394 (8)	C25—C26	1.49 (2)
C9—H9	0.9300	C25—H25A	0.9700
C10—H10	0.9300	C25—H25B	0.9700
C11—C12	1.5 (9)	C26—H26A	0.9600
C11—C12'	1.5 (12)	C26—H26B	0.9600
C11—H11A	0.9700	C26—H26C	0.9600
C11—H11B	0.9700	C25'—C26'	1.52 (7)
C12—C17	1.4 (6)	C25'—H25C	0.9700
C12—C13	1.4 (7)	C25'—H25D	0.9700
C13—C14	1.45 (3)	C26'—H26D	0.9600
C13—H13	0.9300	C26'—H26E	0.9600
C14—C15	1.41 (3)	C26'—H26F	0.9600
C14—H14	0.9300

C11—Sn1—O3	97.42 (19)	C17—C12—C11	121 (10)
C11—Sn1—C18	163.3 (2)	C13—C12—C11	117 (10)
O3—Sn1—C18	94.77 (18)	C12—C13—C14	116 (10)
C11—Sn1—N1	97.9 (2)	C12—C13—H13	122.0
O3—Sn1—N1	70.83 (13)	C14—C13—H13	122.0
C18—Sn1—N1	96.85 (18)	C15—C14—C13	120 (2)
C11—Sn1—O1	88.59 (19)	C15—C14—H14	120.0
O3—Sn1—O1	140.42 (12)	C13—C14—H14	120.0
C18—Sn1—O1	89.30 (18)	C16—C15—C14	123 (3)
N1—Sn1—O1	69.60 (12)	C16—C15—H15	118.3
C11—Sn1—O4	84.9 (2)	C14—C15—H15	118.3
O3—Sn1—O4	78.79 (13)	C15—C16—C17	116 (3)
C18—Sn1—O4	86.28 (19)	C15—C16—H16	122.0
N1—Sn1—O4	149.60 (14)	C17—C16—H16	122.0
O1—Sn1—O4	140.79 (12)	C12—C17—C16	122 (10)
C11—Sn1—O1ⁱ	80.32 (18)	C12—C17—H17	118.8
O3—Sn1—O1ⁱ	154.13 (12)	C16—C17—H17	118.8
C18—Sn1—O1ⁱ	83.72 (16)	C13'—C12'—C17'	120 (10)
N1—Sn1—O1ⁱ	135.04 (12)	C13'—C12'—C11	122.0
O1—Sn1—O1ⁱ	65.45 (12)	C17'—C12'—C11	119.0
O4—Sn1—O1ⁱ	75.34 (11)	C12'—C13'—C14'	121 (10)
C2—N1—N2	120.3 (4)	C12'—C13'—H13'	119.7
C2—N1—Sn1	121.9 (3)	C14'—C13'—H13'	119.7
N2—N1—Sn1	117.7 (3)	C13'—C14'—C15'	118 (3)
C4—N2—N1	109.7 (4)	C13'—C14'—H14'	120.9
C1—O1—Sn1	117.0 (3)	C15'—C14'—H14'	120.9
C4—O3—Sn1	115.9 (3)	C14'—C15'—C16'	122 (4)
C25'—O4—C25	41 (2)	C14'—C15'—H15'	118.9
C25'—O4—Sn1	128.5 (18)	C16'—C15'—H15'	118.9
C25—O4—Sn1	130.5 (5)	C17'—C16'—C15'	118 (4)
C25'—O4—H4	119.4	C17'—C16'—H16'	121.1
C25—O4—H4	104.5	C15'—C16'—H16'	121.1
Sn1—O4—H4	111.7	C16'—C17'—C12'	121 (10)
O2—C1—O1	125.3 (5)	C16'—C17'—H17'	119.7
O2—C1—C2	118.0 (4)	C12'—C17'—H17'	119.7
O1—C1—C2	116.7 (4)	C19—C18—Sn1	113.5 (4)
N1—C2—C3	124.2 (5)	C19—C18—H18A	108.9
N1—C2—C1	114.7 (4)	Sn1—C18—H18A	108.9
C3—C2—C1	121.1 (5)	C19—C18—H18B	108.9
C2—C3—H3A	109.5	Sn1—C18—H18B	108.9
C2—C3—H3B	109.5	H18A—C18—H18B	107.7
H3A—C3—H3B	109.5	C20—C19—C24	118.6 (6)
C2—C3—H3C	109.5	C20—C19—C18	120.8 (5)
H3A—C3—H3C	109.5	C24—C19—C18	120.6 (6)
H3B—C3—H3C	109.5	C19—C20—C21	119.8 (7)
O3—C4—N2	125.9 (4)	C19—C20—H20	120.1
O3—C4—C5	117.2 (5)	C21—C20—H20	120.1
N2—C4—C5	116.9 (5)	C22—C21—C20	119.2 (8)
C10—C5—C6	118.8 (5)	C22—C21—H21	120.4
C10—C5—C4	120.7 (5)	C20—C21—H21	120.4
C6—C5—C4	120.5 (5)	C23—C22—C21	121.5 (7)
C5—C6—C7	120.3 (7)	C23—C22—H22	119.3
C5—C6—H6	119.8	C21—C22—H22	119.3
C7—C6—H6	119.8	C22—C23—C24	120.1 (7)
C8—C7—C6	120.8 (7)	C22—C23—H23	119.9
C8—C7—H7	119.6	C24—C23—H23	119.9
C6—C7—H7	119.6	C23—C24—C19	120.8 (7)
C7—C8—C9	120.4 (6)	C23—C24—H24	119.6
C7—C8—H8	119.8	C19—C24—H24	119.6
C9—C8—H8	119.8	O4—C25—C26	110.9 (11)
C8—C9—C10	119.1 (7)	O4—C25—H25A	109.5
C8—C9—H9	120.5	C26—C25—H25A	109.5
C10—C9—H9	120.5	O4—C25—H25B	109.5
C5—C10—C9	120.6 (6)	C26—C25—H25B	109.5
C5—C10—H10	119.7	H25A—C25—H25B	108.1
C9—C10—H10	119.7	O4—C25'—C26'	111 (4)
C12—C11—C12'	8 (10)	O4—C25'—H25C	109.5
C12—C11—Sn1	116 (10)	C26'—C25'—H25C	109.5
C12'—C11—Sn1	112 (10)	O4—C25'—H25D	109.5
C12—C11—H11A	108.3	C26'—C25'—H25D	109.5
C12'—C11—H11A	104.2	H25C—C25'—H25D	108.1
Sn1—C11—H11A	108.2	C25'—C26'—H26D	109.5
C12—C11—H11B	108.2	C25'—C26'—H26E	109.5
C12'—C11—H11B	119.0	H26D—C26'—H26E	109.5
Sn1—C11—H11B	108.2	C25'—C26'—H26F	109.5
H11A—C11—H11B	107.4	H26D—C26'—H26F	109.5
C17—C12—C13	122 (10)	H26E—C26'—H26F	109.5

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱ	0.82	1.82	2.624 (6)	165

Symmetry code: (i) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Sn₂(C₇H₇)₄(C₁₀H₈N₂O₃)₂(C₂H₆O)₂]
M_r	1102.42
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7187 (18), 11.385 (2), 13.198 (3)
α, β, γ (°)	96.170 (3), 93.728 (2), 105.861 (3)
V (Å³)	1246.8 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.45 × 0.37 × 0.23

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.647, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	6566, 4356, 3598
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.08
No. of reflections	4356
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.58

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

Selected geometric parameters (Å, º) top

Sn1—C11	2.135 (6)	Sn1—O1	2.341 (3)
Sn1—O3	2.148 (3)	Sn1—O4	2.382 (4)
Sn1—C18	2.154 (6)	Sn1—O1ⁱ	2.772 (3)
Sn1—N1	2.237 (4)

C11—Sn1—O3	97.42 (19)	O3—Sn1—O4	78.79 (13)
C11—Sn1—C18	163.3 (2)	C18—Sn1—O4	86.28 (19)
O3—Sn1—C18	94.77 (18)	N1—Sn1—O4	149.60 (14)
C11—Sn1—N1	97.9 (2)	O1—Sn1—O4	140.79 (12)
O3—Sn1—N1	70.83 (13)	C11—Sn1—O1ⁱ	80.32 (18)
C18—Sn1—N1	96.85 (18)	O3—Sn1—O1ⁱ	154.13 (12)
C11—Sn1—O1	88.59 (19)	C18—Sn1—O1ⁱ	83.72 (16)
O3—Sn1—O1	140.42 (12)	N1—Sn1—O1ⁱ	135.04 (12)
C18—Sn1—O1	89.30 (18)	O1—Sn1—O1ⁱ	65.45 (12)
N1—Sn1—O1	69.60 (12)	O4—Sn1—O1ⁱ	75.34 (11)
C11—Sn1—O4	84.9 (2)

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱ	0.82	1.82	2.624 (6)	165

Symmetry code: (i) −x+2, −y+2, −z.

Acknowledgements

We acknowledge financial support by the Clinical Laboratory of Liaocheng Hospital.

References

Gielen, M., Vanbellinghen, C., Gelan, J. & Willem, R. (2002). Bull. Soc. Chim. Belg. 97, 873–878. 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
Sun, L.-N. & Hu, C.-W. (2007). Acta Cryst. E63, m1832–m1833. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page m544

doi:10.1107/S1600536811011937

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

Bis(μ-2-{[oxido(phenyl)methyl­idene]hydrazinyl­idene}propanoato)bis­[di­benzyl(ethanol)tin(IV)]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(μ-2-{[oxido(phenyl)methylidene]hydrazinylidene}propanoato)bis[dibenzyl(ethanol)tin(IV)]