Benzyl­chloridobis(quinolin-8-olato)tin(IV)

Wang, Q.

doi:10.1107/S1600536809025902

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m905

doi:10.1107/S1600536809025902

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Benzylchloridobis(quinolin-8-olato)tin(IV)

Qibao Wang ^a ^*

^aDepartment of Pharmacy, Jining Medical College, No. 669 Xueyuan Road, Rizhao, Shandong 276826, People's Republic of China
^*Correspondence e-mail: qibaowang@mail.jnmc.edu.cn

(Received 12 June 2009; accepted 3 July 2009; online 11 July 2009)

In the title compound, [Sn(C₇H₇)(C₉H₆NO)₂Cl], the Sn^IV ion is in a distorted octahedral coordination environment formed by the O and N atoms of two bis-chelating quinolin-8-olate ligands, a Cl atom and a C atom from a benzyl ligand. The axial sites are occupied by an N atom of a quinolinate ligand and the C atom of the benzyl ligand. The axial Sn—N bond is slightly shorter than the equatorial Sn—N bond.

Related literature

For the chemical, biological and pharmaceutical properties of organotin(IV) complexes, see: Nath et al. (2001 ); Pellerito & Nagy (2002 ). For diorganotin complexes, see: Szorcsik et al. (2005 ). For a related structure, see: Kellö et al. (1995 ).

Experimental

Crystal data

[Sn(C₇H₇)(C₉H₆NO)₂Cl]
M_r = 533.56
Monoclinic, P 2₁ /n
a = 11.6283 (14) Å
b = 10.6290 (14) Å
c = 17.948 (2) Å
β = 94.296 (2)°
V = 2212.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 273 K
0.20 × 0.15 × 0.12 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.781, T_max = 0.860
14242 measured reflections
5410 independent reflections
3930 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.076
S = 1.02
5410 reflections
281 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—O1	2.067 (2)
Sn1—O2	2.074 (2)
Sn1—C19	2.148 (3)
Sn1—N2	2.239 (2)
Sn1—N1	2.252 (2)
Sn1—Cl1	2.4310 (9)

O1—Sn1—O2	154.94 (8)
O1—Sn1—C19	103.86 (12)
O2—Sn1—C19	95.81 (12)
O1—Sn1—N2	85.26 (8)
O2—Sn1—N2	75.96 (8)
C19—Sn1—N2	170.69 (12)
O1—Sn1—N1	76.53 (8)
O2—Sn1—N1	85.38 (8)
C19—Sn1—N1	98.59 (11)
N2—Sn1—N1	85.23 (8)
O1—Sn1—Cl1	91.98 (6)
O2—Sn1—Cl1	102.40 (6)
C19—Sn1—Cl1	93.21 (9)
N2—Sn1—Cl1	84.48 (6)
N1—Sn1—Cl1	165.16 (6)

Data collection: APEX2 (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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025902/lh2848sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025902/lh2848Isup2.hkl

checkCIF report

Comment top

The chemical, biological and pharmaceutical properties of organotin(IV) complexes have been extensively studied owing to their anti-tumor activity( Pellerito & Nagy, 2002; Nath et al., 2001). Organotin(IV) complexes with ligands containing phenolic –OH or phenolic –OH and –COOH groups and an aromatic N donor atom comprise an interesting class of such complexes. The studies are manily focused on diorganotin complexes (Szorcsik et al., 2005) and up until now few publications have been reported on mono-organotin complexes of this type, In this paper, we reported the structure of the title mono-organotin complex. The title compound was synthesized by the reaction of sodium quinolin-8-olate with dibenzyltin dichlorides in dichloromethane. In the title compound, the coordination geometry around the Sn^IV ion is distorted octahedral; two O atoms, a N atom of the cis-chelated 8-quinolinate ligands, and a chlorine atom are in equatorial sites. The axial sites are occupied by the N atom of the other cis-chelate 8-quinolinate group and the C atom of the benzyl group. The two Sn—O distances are the same within experimental error but the axial Sn—N bond is slightly shorter than the equatorial Sn—N bond. The Sn—Cl and Sn—C distances are similar to those in butylchlorobis(8-quinolinate)tin(IV) (Kellö et al., 1995).

Related literature top

For the chemical, biological and pharmaceutical properties of organotin(IV) complexes, see: Nath et al. (2001); Pellerito & Nagy (2002). For diorganotin complexes, see: Szorcsik et al. (2005). For a related structure, see: Kellö et al. (1995).

Experimental top

The mixture of sodium quinolin-8-olate (0.334 g, 2.0 mmol) and dibenzyltin dichlorides (0.372 g, 1.0 mmol) was suspended in 30 ml dichloromethane at room temperature for 24 h, then the sovents were removed on a rotary evaporator, the residue was recrystallized in dichloromethane-hexane (3:1) to give yellow crystals 0.437 g. Yield 82%.

Computing details top

Data collection: APEX2 (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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 30% probability for non-H atoms.

Benzylchloridobis(quinolin-8-olato)tin(IV) top

Crystal data top

[Sn(C₇H₇)(C₉H₆NO)₂Cl]	F(000) = 1064
M_r = 533.56	D_x = 1.602 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3464 reflections
a = 11.6283 (14) Å	θ = 2.2–24.1°
b = 10.6290 (14) Å	µ = 1.30 mm⁻¹
c = 17.948 (2) Å	T = 273 K
β = 94.296 (2)°	Block, yellow
V = 2212.1 (5) Å³	0.20 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	5410 independent reflections
Radiation source: fine-focus sealed tube	3930 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→15
T_min = 0.781, T_max = 0.860	k = −14→9
14242 measured reflections	l = −24→23

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0307P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.002
5410 reflections	Δρ_max = 0.43 e Å⁻³
281 parameters	Δρ_min = −0.39 e Å⁻³
48 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: 0.00054 (14)

Crystal data top

[Sn(C₇H₇)(C₉H₆NO)₂Cl]	V = 2212.1 (5) Å³
M_r = 533.56	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.6283 (14) Å	µ = 1.30 mm⁻¹
b = 10.6290 (14) Å	T = 273 K
c = 17.948 (2) Å	0.20 × 0.15 × 0.12 mm
β = 94.296 (2)°

Data collection top

Bruker APEXII diffractometer	5410 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3930 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.860	R_int = 0.038
14242 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	48 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	Δρ_max = 0.43 e Å⁻³
5410 reflections	Δρ_min = −0.39 e Å⁻³
281 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

	x	y	z	U_iso*/U_eq
Sn1	0.695432 (15)	0.868135 (18)	0.124643 (11)	0.03912 (8)
Cl1	0.65912 (7)	1.09309 (8)	0.12976 (5)	0.0555 (2)
N1	0.69034 (19)	0.6613 (2)	0.09745 (13)	0.0384 (5)
N2	0.50410 (19)	0.8508 (2)	0.12869 (13)	0.0376 (5)
O1	0.66194 (18)	0.86474 (18)	0.00990 (11)	0.0476 (5)
O2	0.67424 (16)	0.8119 (2)	0.23340 (10)	0.0457 (5)
C1	0.7089 (2)	0.5632 (3)	0.14258 (17)	0.0436 (7)
H1	0.7284	0.5771	0.1931	0.052*
C2	0.7000 (2)	0.4408 (3)	0.11637 (18)	0.0529 (8)
H2	0.7139	0.3734	0.1489	0.064*
C3	0.6711 (3)	0.4201 (3)	0.04313 (19)	0.0544 (8)
H3	0.6646	0.3378	0.0256	0.065*
C4	0.6504 (2)	0.5201 (3)	−0.00712 (17)	0.0441 (7)
C5	0.6201 (3)	0.5090 (4)	−0.08445 (19)	0.0595 (9)
H5	0.6123	0.4300	−0.1066	0.071*
C6	0.6023 (3)	0.6147 (4)	−0.12630 (19)	0.0626 (10)
H6	0.5814	0.6065	−0.1771	0.075*
C7	0.6145 (3)	0.7350 (4)	−0.09581 (17)	0.0537 (8)
H7	0.6003	0.8048	−0.1264	0.064*
C8	0.6468 (2)	0.7521 (3)	−0.02160 (16)	0.0419 (7)
C9	0.6630 (2)	0.6424 (3)	0.02335 (15)	0.0374 (6)
C10	0.4226 (2)	0.8810 (3)	0.07682 (17)	0.0454 (7)
H10	0.4433	0.9129	0.0315	0.055*
C11	0.3059 (3)	0.8664 (3)	0.0881 (2)	0.0553 (9)
H11	0.2498	0.8914	0.0515	0.066*
C12	0.2751 (3)	0.8152 (3)	0.1531 (2)	0.0587 (9)
H12	0.1975	0.8036	0.1606	0.070*
C13	0.3607 (2)	0.7794 (3)	0.20950 (18)	0.0479 (7)
C14	0.3386 (3)	0.7245 (4)	0.2775 (2)	0.0685 (10)
H14	0.2634	0.7056	0.2879	0.082*
C15	0.4281 (4)	0.6989 (4)	0.3284 (2)	0.0752 (11)
H15	0.4126	0.6614	0.3734	0.090*
C16	0.5433 (3)	0.7270 (3)	0.31570 (18)	0.0595 (9)
H16	0.6021	0.7095	0.3522	0.071*
C17	0.5684 (2)	0.7800 (3)	0.24933 (16)	0.0428 (7)
C18	0.4754 (2)	0.8027 (3)	0.19468 (16)	0.0388 (6)
C19	0.8792 (2)	0.8914 (3)	0.1398 (2)	0.0616 (10)
H19A	0.9022	0.9534	0.1042	0.074*
H19B	0.8983	0.9249	0.1894	0.074*
C20	0.9480 (2)	0.7754 (3)	0.13088 (17)	0.0453 (7)
C21	0.9725 (3)	0.6970 (4)	0.1901 (2)	0.0668 (10)
H21	0.9468	0.7171	0.2364	0.080*
C22	1.0347 (4)	0.5888 (5)	0.1821 (4)	0.115 (2)
H22	1.0519	0.5367	0.2231	0.138*
C23	1.0711 (5)	0.5578 (6)	0.1143 (5)	0.141 (3)
H23	1.1122	0.4838	0.1086	0.170*
C24	1.0482 (4)	0.6336 (6)	0.0557 (4)	0.118 (2)
H24	1.0742	0.6126	0.0096	0.142*
C25	0.9858 (3)	0.7432 (4)	0.0632 (2)	0.0732 (11)
H25	0.9697	0.7951	0.0221	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03405 (11)	0.03303 (12)	0.04976 (14)	−0.00005 (9)	−0.00043 (8)	−0.00080 (9)
Cl1	0.0532 (4)	0.0332 (4)	0.0790 (6)	0.0005 (3)	−0.0019 (4)	−0.0058 (4)
N1	0.0368 (12)	0.0351 (14)	0.0427 (13)	0.0014 (10)	−0.0021 (10)	−0.0002 (11)
N2	0.0352 (12)	0.0321 (13)	0.0449 (13)	−0.0018 (10)	−0.0021 (10)	−0.0019 (11)
O1	0.0589 (13)	0.0367 (12)	0.0478 (12)	0.0030 (10)	0.0069 (10)	0.0074 (10)
O2	0.0413 (11)	0.0489 (13)	0.0454 (11)	0.0001 (10)	−0.0066 (9)	0.0001 (10)
C1	0.0415 (16)	0.0403 (18)	0.0482 (17)	0.0036 (14)	−0.0016 (13)	0.0021 (14)
C2	0.0550 (19)	0.0406 (18)	0.062 (2)	0.0063 (15)	−0.0037 (16)	0.0055 (16)
C3	0.0527 (18)	0.0365 (18)	0.073 (2)	0.0043 (15)	0.0001 (17)	−0.0106 (17)
C4	0.0350 (14)	0.0447 (18)	0.0523 (18)	0.0044 (13)	0.0012 (13)	−0.0083 (15)
C5	0.059 (2)	0.057 (2)	0.062 (2)	0.0075 (17)	−0.0002 (17)	−0.0210 (18)
C6	0.062 (2)	0.084 (3)	0.0419 (17)	0.013 (2)	0.0022 (15)	−0.0081 (19)
C7	0.056 (2)	0.061 (2)	0.0444 (18)	0.0119 (17)	0.0076 (15)	0.0053 (17)
C8	0.0364 (15)	0.0445 (19)	0.0461 (17)	0.0055 (13)	0.0109 (13)	−0.0015 (14)
C9	0.0315 (13)	0.0369 (16)	0.0440 (16)	0.0036 (12)	0.0042 (12)	−0.0011 (13)
C10	0.0404 (15)	0.0417 (18)	0.0526 (18)	−0.0022 (13)	−0.0063 (13)	0.0058 (14)
C11	0.0379 (16)	0.056 (2)	0.070 (2)	−0.0025 (15)	−0.0126 (15)	0.0040 (18)
C12	0.0385 (17)	0.058 (2)	0.080 (2)	−0.0019 (16)	0.0044 (17)	−0.0098 (19)
C13	0.0395 (16)	0.0464 (19)	0.0586 (19)	−0.0030 (14)	0.0090 (14)	−0.0059 (16)
C14	0.060 (2)	0.081 (3)	0.066 (2)	−0.011 (2)	0.0183 (19)	0.001 (2)
C15	0.088 (3)	0.085 (3)	0.056 (2)	−0.009 (2)	0.024 (2)	0.013 (2)
C16	0.066 (2)	0.065 (2)	0.0467 (19)	0.0048 (18)	−0.0019 (17)	0.0064 (18)
C17	0.0430 (17)	0.0391 (17)	0.0462 (17)	0.0024 (13)	0.0022 (13)	−0.0048 (14)
C18	0.0417 (15)	0.0298 (16)	0.0450 (17)	0.0017 (12)	0.0042 (13)	−0.0062 (13)
C19	0.0335 (16)	0.050 (2)	0.101 (3)	−0.0059 (15)	−0.0019 (17)	−0.0011 (19)
C20	0.0289 (14)	0.0435 (18)	0.063 (2)	−0.0024 (13)	−0.0001 (14)	−0.0020 (16)
C21	0.0453 (19)	0.068 (3)	0.086 (3)	−0.0144 (17)	−0.0035 (18)	0.019 (2)
C22	0.060 (3)	0.063 (3)	0.215 (6)	−0.011 (2)	−0.030 (3)	0.053 (4)
C23	0.060 (3)	0.058 (3)	0.304 (9)	0.005 (3)	−0.001 (5)	−0.045 (4)
C24	0.061 (3)	0.130 (5)	0.167 (5)	−0.014 (3)	0.034 (3)	−0.089 (4)
C25	0.050 (2)	0.101 (3)	0.069 (2)	−0.007 (2)	0.0030 (18)	−0.015 (2)

Geometric parameters (Å, º) top

Sn1—O1	2.067 (2)	C10—H10	0.9300
Sn1—O2	2.074 (2)	C11—C12	1.359 (5)
Sn1—C19	2.148 (3)	C11—H11	0.9300
Sn1—N2	2.239 (2)	C12—C13	1.418 (4)
Sn1—N1	2.252 (2)	C12—H12	0.9300
Sn1—Cl1	2.4310 (9)	C13—C14	1.393 (4)
N1—C1	1.328 (4)	C13—C18	1.401 (4)
N1—C9	1.359 (3)	C14—C15	1.360 (5)
N2—C10	1.318 (3)	C14—H14	0.9300
N2—C18	1.355 (3)	C15—C16	1.408 (5)
O1—C8	1.330 (3)	C15—H15	0.9300
O2—C17	1.328 (3)	C16—C17	1.369 (4)
C1—C2	1.385 (4)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.425 (4)
C2—C3	1.350 (4)	C19—C20	1.485 (4)
C2—H2	0.9300	C19—H19A	0.9700
C3—C4	1.403 (4)	C19—H19B	0.9700
C3—H3	0.9300	C20—C21	1.364 (4)
C4—C5	1.411 (4)	C20—C25	1.366 (4)
C4—C9	1.414 (4)	C21—C22	1.371 (6)
C5—C6	1.359 (5)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.359 (8)
C6—C7	1.394 (5)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.335 (9)
C7—C8	1.369 (4)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.384 (7)
C8—C9	1.422 (4)	C24—H24	0.9300
C10—C11	1.395 (4)	C25—H25	0.9300

O1—Sn1—O2	154.94 (8)	N2—C10—H10	119.1
O1—Sn1—C19	103.86 (12)	C11—C10—H10	119.1
O2—Sn1—C19	95.81 (12)	C12—C11—C10	119.4 (3)
O1—Sn1—N2	85.26 (8)	C12—C11—H11	120.3
O2—Sn1—N2	75.96 (8)	C10—C11—H11	120.3
C19—Sn1—N2	170.69 (12)	C11—C12—C13	120.3 (3)
O1—Sn1—N1	76.53 (8)	C11—C12—H12	119.9
O2—Sn1—N1	85.38 (8)	C13—C12—H12	119.9
C19—Sn1—N1	98.59 (11)	C14—C13—C18	118.7 (3)
N2—Sn1—N1	85.23 (8)	C14—C13—C12	124.9 (3)
O1—Sn1—Cl1	91.98 (6)	C18—C13—C12	116.4 (3)
O2—Sn1—Cl1	102.40 (6)	C15—C14—C13	119.4 (3)
C19—Sn1—Cl1	93.21 (9)	C15—C14—H14	120.3
N2—Sn1—Cl1	84.48 (6)	C13—C14—H14	120.3
N1—Sn1—Cl1	165.16 (6)	C14—C15—C16	122.6 (3)
C1—N1—C9	119.8 (3)	C14—C15—H15	118.7
C1—N1—Sn1	129.3 (2)	C16—C15—H15	118.7
C9—N1—Sn1	110.89 (18)	C17—C16—C15	119.7 (3)
C10—N2—C18	119.9 (2)	C17—C16—H16	120.1
C10—N2—Sn1	128.4 (2)	C15—C16—H16	120.1
C18—N2—Sn1	111.70 (17)	O2—C17—C16	123.6 (3)
C8—O1—Sn1	116.63 (18)	O2—C17—C18	118.4 (3)
C17—O2—Sn1	116.97 (17)	C16—C17—C18	117.9 (3)
N1—C1—C2	121.7 (3)	N2—C18—C13	122.2 (3)
N1—C1—H1	119.1	N2—C18—C17	116.2 (2)
C2—C1—H1	119.1	C13—C18—C17	121.6 (3)
C3—C2—C1	119.4 (3)	C20—C19—Sn1	115.5 (2)
C3—C2—H2	120.3	C20—C19—H19A	108.4
C1—C2—H2	120.3	Sn1—C19—H19A	108.4
C2—C3—C4	121.4 (3)	C20—C19—H19B	108.4
C2—C3—H3	119.3	Sn1—C19—H19B	108.4
C4—C3—H3	119.3	H19A—C19—H19B	107.5
C3—C4—C5	125.9 (3)	C21—C20—C25	118.5 (4)
C3—C4—C9	116.1 (3)	C21—C20—C19	120.4 (3)
C5—C4—C9	117.9 (3)	C25—C20—C19	121.1 (3)
C6—C5—C4	119.4 (3)	C20—C21—C22	120.8 (4)
C6—C5—H5	120.3	C20—C21—H21	119.6
C4—C5—H5	120.3	C22—C21—H21	119.6
C5—C6—C7	122.3 (3)	C23—C22—C21	119.9 (6)
C5—C6—H6	118.8	C23—C22—H22	120.0
C7—C6—H6	118.8	C21—C22—H22	120.0
C8—C7—C6	121.1 (3)	C24—C23—C22	120.1 (6)
C8—C7—H7	119.5	C24—C23—H23	120.0
C6—C7—H7	119.5	C22—C23—H23	120.0
O1—C8—C7	123.5 (3)	C23—C24—C25	120.4 (6)
O1—C8—C9	119.3 (3)	C23—C24—H24	119.8
C7—C8—C9	117.3 (3)	C25—C24—H24	119.8
N1—C9—C4	121.6 (3)	C20—C25—C24	120.2 (5)
N1—C9—C8	116.4 (3)	C20—C25—H25	119.9
C4—C9—C8	121.9 (3)	C24—C25—H25	119.9
N2—C10—C11	121.7 (3)

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₇)(C₉H₆NO)₂Cl]
M_r	533.56
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	11.6283 (14), 10.6290 (14), 17.948 (2)
β (°)	94.296 (2)
V (Å³)	2212.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.20 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.781, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	14242, 5410, 3930
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.076, 1.02
No. of reflections	5410
No. of parameters	281
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Sn1—O1	2.067 (2)	Sn1—N2	2.239 (2)
Sn1—O2	2.074 (2)	Sn1—N1	2.252 (2)
Sn1—C19	2.148 (3)	Sn1—Cl1	2.4310 (9)

O1—Sn1—O2	154.94 (8)	C19—Sn1—N1	98.59 (11)
O1—Sn1—C19	103.86 (12)	N2—Sn1—N1	85.23 (8)
O2—Sn1—C19	95.81 (12)	O1—Sn1—Cl1	91.98 (6)
O1—Sn1—N2	85.26 (8)	O2—Sn1—Cl1	102.40 (6)
O2—Sn1—N2	75.96 (8)	C19—Sn1—Cl1	93.21 (9)
C19—Sn1—N2	170.69 (12)	N2—Sn1—Cl1	84.48 (6)
O1—Sn1—N1	76.53 (8)	N1—Sn1—Cl1	165.16 (6)
O2—Sn1—N1	85.38 (8)

Acknowledgements

This work was supported by the S&R Project–Starting Off Funds of JMC.

References

Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kellö, E., Vrábel, V., Holeček, J. & Sivý, J. (1995). J. Organomet. Chem. 493, 13–16. CSD CrossRef Web of Science Google Scholar
Nath, Y., Pokharia, S. & Yadav, R. (2001). Coord. Chem. Rev. 215, 99–149. Web of Science CrossRef CAS Google Scholar
Pellerito, L. L. & Nagy, L. (2002). Coord. Chem. Rev. 224, 111–150. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szorcsik, A., Nagy, L., Scopelliti, M., Deàk, A., Pellerito, L. & Hegetschweiler, K. (2005). J. Organomet. Chem. 690, 2243–2253. Web of Science CSD CrossRef CAS Google Scholar