[5-Chloro-2-hy­droxy-N′-(2-oxidobenzyl­idene)benzohydrazidato]dimethyl­tin(IV)

Zhang, X.; Yue, C.; Yin, H.

doi:10.1107/S1600536811025621

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1028

doi:10.1107/S1600536811025621

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[5-Chloro-2-hydroxy-N′-(2-oxidobenzylidene)benzohydrazidato]dimethyltin(IV)

Xiuyun Zhang,^a Caihong Yue ^a and Handong Yin ^a ^*

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

(Received 6 June 2011; accepted 29 June 2011; online 6 July 2011)

In the title compound, [Sn(CH₃)₂(C₁₄H₉ClN₂O₃)], the Sn^IV ion is coordinated by one N and two O atoms from the tridentate 5-chloro-2-hydroxy-N′-(2-oxidobenzylidene)benzohydrazidate (L) ligand and two methyl groups in a distorted trigonal–bipyramidal geometry. In the ligand, the hydroxy group is involved in an intramolecular O—H⋯N hydrogen bond and the two aromatic rings form a dihedral angle of 5.5 (1)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds and π–π interactions between the aromatic rings [centroid–centroid distance = 3.816 (3) Å] link the molecules into centrosymmetric dimers.

Related literature

For related structures, see: Yearwood et al. (2002 ); Hong et al. (2010 ); Li et al. (2009 ).

Experimental

Crystal data

[Sn(CH₃)₂(C₁₄H₉ClN₂O₃)]
M_r = 437.44
Monoclinic, P 2₁ /c
a = 7.5096 (5) Å
b = 20.965 (2) Å
c = 10.8344 (11) Å
β = 95.634 (1)°
V = 1697.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.68 mm⁻¹
T = 298 K
0.48 × 0.41 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.500, T_max = 0.699
8414 measured reflections
2975 independent reflections
2357 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.071
S = 1.07
2975 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1ⁱ	0.96	2.59	3.430 (5)	147
O1—H1⋯N1	0.82	1.87	2.577 (4)	144
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536811025621/cv5115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025621/cv5115Isup2.hkl

checkCIF report

Comment top

Organotin(IV) compounds of hydrazone Schiff bases were reported by Hong et al. (2010). In continuation of our study of hydrazone Schiff base organotin(IV) compounds (Li et al., 2009), we have synthesized the title compound, (I).

In (I) (Fig. 1), the tin center is five-coordinated in a distorted trigonal bipyramidal geometry, being surrounded by two C atoms from the alkyl and one N atom, two O atoms from the Schiff base ligand. So the ligand coordinated to the tin atom as a tridentate ligand. In the tridentate ligand, two aromatic rings form a dihedral angle of 5.5 (1)°. The O atoms coordinate the Sn center with different bond lengths - for carbonyl O2 atom Sn—O2 = 2.183 (2) Å, and for hydroxy O3 atom Sn—O3 = 2.078 (3) Å. Similar structural parameters were observed in the related compound (Yearwood et al., 2002). In (I), the angles o C15–Sn–C16, C15–Sn–O3 and C16–Sn–O3 are 129.30 (15)°, 100.22 (14)° and 95.08 (14)°, respectively, indicating the distorted trigonal bipyramidal coordination geometry.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) and π—π interactions between the aromatic rings [centroid-to-centroid distance of 3.816 (3) Å] link the molecules into centrosymmetric dimers (Fig.2 ).

Related literature top

For related structures, see: Yearwood et al. (2002); Hong et al. (2010); Li et al. (2009).

Experimental top

The reaction was carried out under nitrogen atmosphere. The Schiff base ligand (0.2 mmol) was added to 30 ml e thanol with sodium ethoxide (0.4 mmol). The mixture was stirred for 0.5 h and then dichlorodimethyltin (0.2 mmol) was added.And 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-petroleum ether (1:1, v/v). Anal. Calcd (%) for C₁₆H₁₅Cl_N2_O3_Sn (Mr = 437.44): C, 43.93; H, 3.46; N, 6.40; O, 10.97. Found (%): C, 43.90; H, 3.42; N, 6.35; O, 10.9.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (I) showing the atomic numbering and 50% probability displacement ellipsoids.
	Fig. 2. Centrosymmetric dimer in the crystal structure of (I) [symmetry code: (a) - x + 1,-y + 1,-z + 1]. Dashed lines denote intermolecular C—H···O hydrogen bonds and π—π interactions.

[5-Chloro-2-hydroxy-N'-(2- oxidobenzylidene)benzohydrazidato]dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₄H₉ClN₂O₃)]	F(000) = 864
M_r = 437.44	D_x = 1.712 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5096 (5) Å	Cell parameters from 4020 reflections
b = 20.965 (2) Å	θ = 3.3–27.2°
c = 10.8344 (11) Å	µ = 1.68 mm⁻¹
β = 95.634 (1)°	T = 298 K
V = 1697.5 (3) Å³	Block, yellow
Z = 4	0.48 × 0.41 × 0.23 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2975 independent reflections
Radiation source: fine-focus sealed tube	2357 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.500, T_max = 0.699	k = −24→23
8414 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.026P)² + 0.2305P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2975 reflections	Δρ_max = 0.44 e Å⁻³
212 parameters	Δρ_min = −0.67 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0182 (6)

Crystal data top

[Sn(CH₃)₂(C₁₄H₉ClN₂O₃)]	V = 1697.5 (3) Å³
M_r = 437.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5096 (5) Å	µ = 1.68 mm⁻¹
b = 20.965 (2) Å	T = 298 K
c = 10.8344 (11) Å	0.48 × 0.41 × 0.23 mm
β = 95.634 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2975 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2357 reflections with I > 2σ(I)
T_min = 0.500, T_max = 0.699	R_int = 0.052
8414 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.07	Δρ_max = 0.44 e Å⁻³
2975 reflections	Δρ_min = −0.67 e Å⁻³
212 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.36782 (3)	0.466514 (11)	0.80395 (2)	0.03921 (13)
Cl1	−0.1037 (2)	0.21038 (5)	0.43753 (11)	0.0807 (4)
N1	0.2415 (4)	0.48410 (14)	0.5277 (3)	0.0413 (7)
N2	0.3277 (4)	0.51754 (13)	0.6279 (3)	0.0365 (7)
O1	0.1173 (5)	0.46606 (13)	0.3001 (2)	0.0606 (8)
H1	0.1802	0.4835	0.3564	0.091*
O2	0.2336 (4)	0.40168 (12)	0.6672 (2)	0.0498 (7)
O3	0.4514 (4)	0.55533 (12)	0.8723 (2)	0.0534 (7)
C1	0.1973 (5)	0.42608 (17)	0.5585 (3)	0.0369 (8)
C2	0.1016 (5)	0.38655 (16)	0.4607 (3)	0.0372 (8)
C3	0.0701 (5)	0.40754 (18)	0.3373 (3)	0.0413 (9)
C4	−0.0106 (5)	0.36639 (19)	0.2477 (3)	0.0501 (10)
H4	−0.0283	0.3799	0.1656	0.060*
C5	−0.0637 (6)	0.30721 (19)	0.2777 (3)	0.0492 (10)
H5	−0.1184	0.2805	0.2168	0.059*
C6	−0.0362 (5)	0.28668 (17)	0.3994 (3)	0.0455 (9)
C7	0.0456 (5)	0.32594 (17)	0.4898 (3)	0.0407 (9)
H7	0.0635	0.3116	0.5713	0.049*
C8	0.3792 (5)	0.57425 (17)	0.6034 (3)	0.0409 (9)
H8	0.3597	0.5870	0.5210	0.049*
C9	0.4634 (5)	0.62022 (16)	0.6886 (3)	0.0405 (9)
C10	0.5084 (5)	0.67917 (18)	0.6401 (4)	0.0532 (10)
H10	0.4906	0.6858	0.5549	0.064*
C11	0.5786 (6)	0.72764 (19)	0.7158 (4)	0.0607 (12)
H11	0.6094	0.7666	0.6826	0.073*
C12	0.6020 (6)	0.7170 (2)	0.8418 (4)	0.0611 (12)
H12	0.6478	0.7497	0.8936	0.073*
C13	0.5603 (6)	0.66031 (19)	0.8930 (4)	0.0554 (11)
H13	0.5786	0.6551	0.9785	0.066*
C14	0.4897 (5)	0.60941 (18)	0.8185 (3)	0.0444 (9)
C15	0.6154 (5)	0.41890 (19)	0.8108 (4)	0.0536 (10)
H15A	0.6874	0.4378	0.7521	0.080*
H15B	0.5956	0.3747	0.7907	0.080*
H15C	0.6761	0.4224	0.8927	0.080*
C16	0.1613 (6)	0.45669 (19)	0.9204 (4)	0.0528 (11)
H16A	0.2094	0.4617	1.0052	0.079*
H16B	0.1083	0.4152	0.9091	0.079*
H16C	0.0719	0.4887	0.8999	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0436 (2)	0.03337 (18)	0.04025 (17)	−0.00176 (11)	0.00207 (11)	0.00346 (11)
Cl1	0.1181 (11)	0.0464 (7)	0.0724 (8)	−0.0281 (7)	−0.0178 (7)	0.0042 (6)
N1	0.049 (2)	0.0347 (17)	0.0402 (16)	−0.0027 (14)	0.0022 (14)	0.0004 (14)
N2	0.0372 (18)	0.0300 (16)	0.0424 (16)	0.0005 (13)	0.0037 (13)	0.0041 (13)
O1	0.087 (2)	0.0491 (18)	0.0438 (16)	−0.0106 (15)	−0.0039 (15)	0.0111 (13)
O2	0.0696 (19)	0.0399 (15)	0.0378 (14)	−0.0116 (14)	−0.0056 (13)	0.0044 (12)
O3	0.078 (2)	0.0340 (14)	0.0468 (15)	−0.0133 (14)	0.0014 (14)	0.0037 (13)
C1	0.035 (2)	0.037 (2)	0.040 (2)	0.0052 (16)	0.0058 (16)	0.0016 (16)
C2	0.036 (2)	0.038 (2)	0.0373 (19)	0.0063 (16)	0.0004 (15)	−0.0022 (16)
C3	0.045 (2)	0.036 (2)	0.043 (2)	0.0046 (17)	0.0081 (17)	0.0042 (17)
C4	0.057 (3)	0.054 (3)	0.038 (2)	0.000 (2)	−0.0014 (18)	−0.0012 (19)
C5	0.053 (3)	0.050 (2)	0.044 (2)	0.001 (2)	−0.0006 (18)	−0.0085 (19)
C6	0.050 (3)	0.038 (2)	0.047 (2)	−0.0004 (18)	0.0005 (18)	−0.0006 (17)
C7	0.043 (2)	0.042 (2)	0.0366 (19)	0.0005 (17)	−0.0003 (16)	0.0010 (17)
C8	0.042 (2)	0.036 (2)	0.047 (2)	0.0040 (17)	0.0100 (17)	0.0106 (17)
C9	0.039 (2)	0.030 (2)	0.054 (2)	0.0014 (16)	0.0118 (18)	0.0011 (17)
C10	0.056 (3)	0.038 (2)	0.066 (3)	0.0014 (19)	0.010 (2)	0.008 (2)
C11	0.063 (3)	0.033 (2)	0.089 (3)	−0.007 (2)	0.020 (3)	0.001 (2)
C12	0.058 (3)	0.044 (3)	0.082 (3)	−0.011 (2)	0.009 (2)	−0.011 (2)
C13	0.064 (3)	0.041 (2)	0.061 (3)	−0.007 (2)	0.004 (2)	−0.008 (2)
C14	0.040 (2)	0.038 (2)	0.056 (2)	0.0007 (18)	0.0088 (18)	−0.0022 (19)
C15	0.050 (3)	0.047 (2)	0.064 (3)	0.009 (2)	0.007 (2)	0.010 (2)
C16	0.052 (3)	0.062 (3)	0.045 (2)	0.001 (2)	0.0056 (19)	0.0049 (19)

Geometric parameters (Å, º) top

Sn1—O3	2.078 (3)	C6—C7	1.378 (5)
Sn1—C16	2.103 (4)	C7—H7	0.9300
Sn1—C15	2.105 (4)	C8—C9	1.437 (5)
Sn1—N2	2.182 (3)	C8—H8	0.9300
Sn1—O2	2.183 (2)	C9—C10	1.398 (5)
Cl1—C6	1.740 (4)	C9—C14	1.420 (5)
N1—C1	1.312 (4)	C10—C11	1.377 (6)
N1—N2	1.397 (4)	C10—H10	0.9300
N2—C8	1.286 (4)	C11—C12	1.377 (6)
O1—C3	1.349 (4)	C11—H11	0.9300
O1—H1	0.8200	C12—C13	1.362 (6)
O2—C1	1.288 (4)	C12—H12	0.9300
O3—C14	1.319 (4)	C13—C14	1.409 (5)
C1—C2	1.476 (5)	C13—H13	0.9300
C2—C7	1.385 (5)	C15—H15A	0.9600
C2—C3	1.405 (5)	C15—H15B	0.9600
C3—C4	1.393 (5)	C15—H15C	0.9600
C4—C5	1.353 (5)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.383 (5)	C16—H16C	0.9600
C5—H5	0.9300	CG1—CG2ⁱ	3.8154 (2)

O3—Sn1—C16	95.08 (14)	C6—C7—H7	119.7
O3—Sn1—C15	100.23 (14)	C2—C7—H7	119.7
C16—Sn1—C15	129.29 (15)	N2—C8—C9	127.6 (3)
O3—Sn1—N2	83.30 (10)	N2—C8—H8	116.2
C16—Sn1—N2	121.70 (13)	C9—C8—H8	116.2
C15—Sn1—N2	108.00 (13)	C10—C9—C14	119.9 (3)
O3—Sn1—O2	154.56 (10)	C10—C9—C8	117.3 (3)
C16—Sn1—O2	91.59 (13)	C14—C9—C8	122.6 (3)
C15—Sn1—O2	94.35 (13)	C11—C10—C9	121.4 (4)
N2—Sn1—O2	72.36 (10)	C11—C10—H10	119.3
C1—N1—N2	112.1 (3)	C9—C10—H10	119.3
C8—N2—N1	115.4 (3)	C12—C11—C10	118.4 (4)
C8—N2—Sn1	128.0 (2)	C12—C11—H11	120.8
N1—N2—Sn1	116.6 (2)	C10—C11—H11	120.8
C3—O1—H1	109.5	C13—C12—C11	122.2 (4)
C1—O2—Sn1	114.5 (2)	C13—C12—H12	118.9
C14—O3—Sn1	133.1 (2)	C11—C12—H12	118.9
O2—C1—N1	124.4 (3)	C12—C13—C14	121.1 (4)
O2—C1—C2	118.6 (3)	C12—C13—H13	119.4
N1—C1—C2	117.1 (3)	C14—C13—H13	119.4
C7—C2—C3	118.6 (3)	O3—C14—C13	118.9 (3)
C7—C2—C1	119.3 (3)	O3—C14—C9	124.0 (3)
C3—C2—C1	122.1 (3)	C13—C14—C9	117.0 (4)
O1—C3—C4	117.7 (3)	Sn1—C15—H15A	109.5
O1—C3—C2	123.0 (3)	Sn1—C15—H15B	109.5
C4—C3—C2	119.4 (4)	H15A—C15—H15B	109.5
C5—C4—C3	121.3 (4)	Sn1—C15—H15C	109.5
C5—C4—H4	119.4	H15A—C15—H15C	109.5
C3—C4—H4	119.4	H15B—C15—H15C	109.5
C4—C5—C6	119.6 (4)	Sn1—C16—H16A	109.5
C4—C5—H5	120.2	Sn1—C16—H16B	109.5
C6—C5—H5	120.2	H16A—C16—H16B	109.5
C7—C6—C5	120.4 (4)	Sn1—C16—H16C	109.5
C7—C6—Cl1	120.0 (3)	H16A—C16—H16C	109.5
C5—C6—Cl1	119.5 (3)	H16B—C16—H16C	109.5
C6—C7—C2	120.7 (3)

C1—N1—N2—C8	178.1 (3)	C7—C2—C3—C4	−2.1 (5)
C1—N1—N2—Sn1	0.5 (4)	C1—C2—C3—C4	175.8 (3)
O3—Sn1—N2—C8	10.7 (3)	O1—C3—C4—C5	−179.2 (4)
C16—Sn1—N2—C8	102.5 (3)	C2—C3—C4—C5	1.8 (6)
C15—Sn1—N2—C8	−87.9 (3)	C3—C4—C5—C6	−0.6 (6)
O2—Sn1—N2—C8	−176.8 (3)	C4—C5—C6—C7	−0.4 (6)
O3—Sn1—N2—N1	−172.0 (2)	C4—C5—C6—Cl1	−179.7 (3)
C16—Sn1—N2—N1	−80.1 (3)	C5—C6—C7—C2	0.1 (6)
C15—Sn1—N2—N1	89.4 (3)	Cl1—C6—C7—C2	179.4 (3)
O2—Sn1—N2—N1	0.5 (2)	C3—C2—C7—C6	1.2 (5)
O3—Sn1—O2—C1	16.0 (4)	C1—C2—C7—C6	−176.8 (3)
C16—Sn1—O2—C1	121.4 (3)	N1—N2—C8—C9	177.0 (3)
C15—Sn1—O2—C1	−109.0 (3)	Sn1—N2—C8—C9	−5.6 (5)
N2—Sn1—O2—C1	−1.5 (2)	N2—C8—C9—C10	179.8 (4)
C16—Sn1—O3—C14	−132.8 (4)	N2—C8—C9—C14	−4.8 (6)
C15—Sn1—O3—C14	95.7 (4)	C14—C9—C10—C11	0.1 (6)
N2—Sn1—O3—C14	−11.5 (4)	C8—C9—C10—C11	175.6 (4)
O2—Sn1—O3—C14	−28.3 (5)	C9—C10—C11—C12	−0.7 (6)
Sn1—O2—C1—N1	2.6 (4)	C10—C11—C12—C13	0.9 (7)
Sn1—O2—C1—C2	−178.2 (2)	C11—C12—C13—C14	−0.3 (7)
N2—N1—C1—O2	−2.1 (5)	Sn1—O3—C14—C13	−174.0 (3)
N2—N1—C1—C2	178.7 (3)	Sn1—O3—C14—C9	6.4 (6)
O2—C1—C2—C7	3.3 (5)	C12—C13—C14—O3	180.0 (4)
N1—C1—C2—C7	−177.4 (3)	C12—C13—C14—C9	−0.4 (6)
O2—C1—C2—C3	−174.6 (3)	C10—C9—C14—O3	−179.9 (4)
N1—C1—C2—C3	4.8 (5)	C8—C9—C14—O3	4.8 (6)
C7—C2—C3—O1	179.0 (3)	C10—C9—C14—C13	0.5 (5)
C1—C2—C3—O1	−3.1 (5)	C8—C9—C14—C13	−174.8 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1ⁱ	0.96	2.59	3.430 (5)	147
O1—H1···N1	0.82	1.87	2.577 (4)	144

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₄H₉ClN₂O₃)]
M_r	437.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.5096 (5), 20.965 (2), 10.8344 (11)
β (°)	95.634 (1)
V (Å³)	1697.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.68
Crystal size (mm)	0.48 × 0.41 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.500, 0.699
No. of measured, independent and observed [I > 2σ(I)] reflections	8414, 2975, 2357
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.071, 1.07
No. of reflections	2975
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.67

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1ⁱ	0.96	2.59	3.430 (5)	147
O1—H1···N1	0.82	1.87	2.577 (4)	144

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hong, M., Yin, H.-D., Chen, S.-W. & Wang, D.-Q. (2010). J. Organomet. Chem. 695, 653–662. Web of Science CSD CrossRef CAS Google Scholar
Li, J., Yin, H., Wen, L. & Cui, J. (2009). Acta Cryst. E65, m1441. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yearwood, 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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Volume 67| Part 8| August 2011| Page m1028

doi:10.1107/S1600536811025621

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

[5-Chloro-2-hy­dr­oxy-N′-(2-oxido­benzyl­­idene)benzohydrazidato]di­methyl­tin(IV)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[5-Chloro-2-hydroxy-N′-(2-oxidobenzylidene)benzohydrazidato]dimethyltin(IV)