Bis(μ-quinolin-8-olato)-κ³ N,O:O;κ³ O:N,O-bis­[chloridomethyl­phenyl­tin(IV)]

Abstract

The Sn^IV atom in the centrosymmetric dinculear title compound, [Sn₂(CH₃)₂(C₆H₅)₂(C₉H₆NO)₂Cl₂], shows a trans-C₂SnNO₂Cl distorted octa­hedral coordination [C–Sn–C = 157.83 (8)°]. The quinolin-8-olate anion chelates to the Sn atom; its O atom also binds to the inversion-related Sn atom, forming the dinuclear compound. In the crystal structure, weak inter­molecular C—H⋯Cl hydrogen bonding links the mol­ecules, forming supra­molecular chains running along [100].

Related literature

For related structures, see: Ng et al. (1989 ▶); Shi & Hu (1987 ▶).

Experimental

Crystal data

• [Sn₂(CH₃)₂(C₆H₅)₂(C₉H₆NO)₂Cl₂]

• M _r = 780.84

• Monoclinic,

• a = 7.9967 (5) Å

• b = 17.8081 (10) Å

• c = 10.1623 (6) Å

• β = 95.232 (1)°

• V = 1441.14 (15) ų

• Z = 2

• Mo Kα radiation

• μ = 1.95 mm⁻¹

• T = 100 K

• 0.30 × 0.20 × 0.10 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.592, T _max = 0.829

• 9127 measured reflections

• 3245 independent reflections

• 3088 reflections with I > 2σ(I)

• R _int = 0.017

Refinement

• R[F ² > 2σ(F ²)] = 0.018

• wR(F ²) = 0.047

• S = 1.09

• 3245 reflections

• 182 parameters

• H-atom parameters constrained

• Δρ_max = 0.43 e Å⁻³

• Δρ_min = −0.52 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cl1i	0.95	2.76	3.710 (2)	174

Symmetry code: (i) .

supplementary crystallographic information

Comment

The anion of 8-hydroxyquinoline is known to chelate to tin in organotin(IV) quinolinolates; however, for the chloroorganotin quinolinates, the chlorine atom sometimes participates in weak intermolecular bridging. In chloridoodiethyl(quinolin-8-olato)tin, the carbon–tin–carbon angle is opened to 140.9 (3) ° owing to a tin···chlorine contact of 3.690 (2) Å (Shi & Hu, 1987). With the bis(2-carbomethoxyethyl) analog, the tin atom is six-coordinate owing to an intramolecular bond with the oxygen atom of the organo radical (Ng et al., 1989). The chloridomethylphenyltin analog exists as a centrosymmetric dimer in which the quinolin-8-olate anion N,O-chelates to the tin atom (Fig. 1). However, its oxygen atom also binds to the inversion-related tin atom so that bridging by the chlorine atom is precluded for the trans-C₂SnNO₂Cl octahedral dinuclear molecule. Intermolecular weak C—H···Cl hydrogen bonding links the molecules to form the one dimensional supra-molecular chain in the crystal structure (Table 1).

Experimental

Methylphenyltin dichloride (0.35 g, 1 mmol) and 8-hydroxyquinoline (0.15 g, 1 mmol) were dissolved in methanol (10 ml) to give a faint yellow solution. The solution was set aside for the growth of crystals over a few days. Slow evaporation of methanol furnished crystals.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U_eq(C).

The final difference Fourier map had a peak in the vicinity of Sn1.

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of [SnCl(CH3)(C6H5)(C9H6NO)]2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn2(CH3)2(C6H5)2(C9H6NO)2Cl2]	F(000) = 768
Mr = 780.84	Dx = 1.799 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6739 reflections
a = 7.9967 (5) Å	θ = 2.3–28.3°
b = 17.8081 (10) Å	µ = 1.95 mm−1
c = 10.1623 (6) Å	T = 100 K
β = 95.232 (1)°	Block, yellow
V = 1441.14 (15) Å3	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer	3245 independent reflections
Radiation source: fine-focus sealed tube	3088 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→6
Tmin = 0.592, Tmax = 0.829	k = −23→23
9127 measured reflections	l = −12→12

Refinement

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.021P)2 + 1.1915P] where P = (Fo2 + 2Fc2)/3
3245 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.569331 (15)	0.585876 (6)	0.601796 (12)	0.01090 (5)
Cl1	0.70000 (6)	0.71504 (2)	0.65698 (5)	0.01757 (10)
O1	0.42527 (16)	0.48265 (7)	0.60854 (13)	0.0135 (3)
N1	0.4714 (2)	0.58459 (8)	0.80183 (16)	0.0121 (3)
C1	0.8095 (2)	0.53633 (10)	0.6389 (2)	0.0167 (4)
H1A	0.7981	0.4816	0.6403	0.025*
H1B	0.8618	0.5536	0.7245	0.025*
H1C	0.8800	0.5508	0.5691	0.025*
C2	0.3678 (2)	0.64342 (9)	0.49452 (19)	0.0130 (4)
C3	0.3885 (3)	0.67691 (11)	0.3733 (2)	0.0169 (4)
H3	0.4928	0.6723	0.3361	0.020*
C4	0.2584 (3)	0.71696 (11)	0.3060 (2)	0.0195 (4)
H4	0.2734	0.7388	0.2226	0.023*
C5	0.1060 (3)	0.72510 (11)	0.3607 (2)	0.0207 (4)
H5	0.0176	0.7533	0.3156	0.025*
C6	0.0837 (3)	0.69195 (11)	0.4814 (2)	0.0206 (4)
H6	−0.0198	0.6975	0.5194	0.025*
C7	0.2136 (2)	0.65061 (10)	0.5464 (2)	0.0164 (4)
H7	0.1967	0.6268	0.6279	0.020*
C8	0.3633 (2)	0.52614 (10)	0.81865 (18)	0.0119 (3)
C9	0.3396 (2)	0.47262 (10)	0.71380 (18)	0.0124 (3)
C10	0.2317 (2)	0.41329 (10)	0.7296 (2)	0.0147 (4)
H10	0.2124	0.3772	0.6611	0.018*
C11	0.1502 (2)	0.40557 (10)	0.8459 (2)	0.0173 (4)
H11	0.0772	0.3641	0.8544	0.021*
C12	0.1735 (2)	0.45627 (10)	0.9470 (2)	0.0162 (4)
H12	0.1177	0.4497	1.0248	0.019*
C13	0.2812 (2)	0.51873 (10)	0.93531 (19)	0.0133 (4)
C14	0.3148 (3)	0.57403 (11)	1.0345 (2)	0.0160 (4)
H14	0.2616	0.5713	1.1142	0.019*
C15	0.4242 (2)	0.63159 (10)	1.0154 (2)	0.0165 (4)
H15	0.4471	0.6688	1.0816	0.020*
C16	0.5016 (2)	0.63503 (10)	0.89730 (19)	0.0146 (4)
H16	0.5781	0.6747	0.8851	0.018*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Sn1	0.01182 (7)	0.01028 (7)	0.01071 (8)	0.00014 (4)	0.00166 (5)	0.00028 (4)
Cl1	0.0161 (2)	0.01251 (19)	0.0241 (3)	−0.00307 (15)	0.00144 (18)	−0.00177 (16)
O1	0.0167 (6)	0.0120 (6)	0.0123 (7)	−0.0016 (5)	0.0041 (5)	−0.0008 (5)
N1	0.0147 (8)	0.0107 (7)	0.0110 (8)	0.0009 (5)	0.0018 (6)	0.0001 (5)
C1	0.0155 (9)	0.0161 (8)	0.0185 (10)	0.0022 (7)	0.0006 (7)	−0.0006 (7)
C2	0.0149 (9)	0.0093 (7)	0.0144 (9)	−0.0004 (6)	−0.0006 (7)	−0.0027 (6)
C3	0.0181 (9)	0.0157 (8)	0.0170 (10)	0.0016 (7)	0.0027 (8)	−0.0005 (7)
C4	0.0269 (11)	0.0179 (9)	0.0133 (10)	0.0027 (8)	−0.0012 (8)	0.0020 (7)
C5	0.0206 (10)	0.0178 (9)	0.0221 (11)	0.0035 (7)	−0.0064 (8)	−0.0015 (8)
C6	0.0146 (9)	0.0228 (10)	0.0242 (11)	0.0002 (7)	0.0009 (8)	−0.0043 (8)
C7	0.0179 (9)	0.0182 (9)	0.0131 (10)	−0.0013 (7)	0.0014 (7)	−0.0010 (7)
C8	0.0128 (8)	0.0120 (8)	0.0107 (9)	0.0014 (6)	0.0005 (7)	0.0015 (6)
C9	0.0125 (8)	0.0125 (8)	0.0121 (9)	0.0027 (6)	0.0007 (7)	0.0012 (7)
C10	0.0154 (9)	0.0127 (8)	0.0159 (10)	−0.0003 (6)	0.0006 (7)	−0.0013 (7)
C11	0.0147 (9)	0.0143 (8)	0.0232 (11)	−0.0018 (7)	0.0030 (8)	0.0026 (7)
C12	0.0149 (9)	0.0178 (9)	0.0169 (10)	0.0018 (7)	0.0057 (7)	0.0032 (7)
C13	0.0135 (9)	0.0145 (8)	0.0122 (9)	0.0030 (6)	0.0019 (7)	0.0002 (7)
C14	0.0207 (10)	0.0196 (9)	0.0084 (9)	0.0042 (7)	0.0045 (7)	−0.0001 (7)
C15	0.0208 (10)	0.0157 (8)	0.0128 (10)	0.0035 (7)	−0.0001 (8)	−0.0033 (7)
C16	0.0155 (9)	0.0132 (8)	0.0148 (10)	0.0007 (7)	−0.0003 (7)	−0.0010 (7)

Geometric parameters (Å, °)

Sn1—C1	2.1162 (19)	C5—H5	0.9500
Sn1—C2	2.1248 (18)	C6—C7	1.390 (3)
Sn1—O1	2.1739 (13)	C6—H6	0.9500
Sn1—O1i	2.4651 (13)	C7—H7	0.9500
Sn1—N1	2.2442 (16)	C8—C13	1.413 (3)
Sn1—Cl1	2.5672 (5)	C8—C9	1.429 (2)
O1—C9	1.334 (2)	C9—C10	1.383 (3)
O1—Sn1i	2.4651 (13)	C10—C11	1.408 (3)
N1—C16	1.328 (2)	C10—H10	0.9500
N1—C8	1.373 (2)	C11—C12	1.367 (3)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.419 (3)
C1—H1C	0.9800	C12—H12	0.9500
C2—C3	1.392 (3)	C13—C14	1.417 (3)
C2—C7	1.391 (3)	C14—C15	1.373 (3)
C3—C4	1.388 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.401 (3)
C4—C5	1.393 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.387 (3)
C1—Sn1—C2	157.83 (8)	C6—C5—C4	119.75 (19)
C1—Sn1—O1	96.71 (6)	C6—C5—H5	120.1
C2—Sn1—O1	92.56 (6)	C4—C5—H5	120.1
C1—Sn1—N1	102.73 (7)	C5—C6—C7	119.69 (19)
C2—Sn1—N1	99.13 (7)	C5—C6—H6	120.2
O1—Sn1—N1	74.52 (5)	C7—C6—H6	120.2
C1—Sn1—O1i	81.99 (6)	C2—C7—C6	121.21 (19)
C2—Sn1—O1i	82.31 (6)	C2—C7—H7	119.4
O1—Sn1—O1i	70.12 (5)	C6—C7—H7	119.4
N1—Sn1—O1i	144.64 (5)	N1—C8—C13	121.40 (16)
C1—Sn1—Cl1	89.42 (5)	N1—C8—C9	117.06 (16)
C2—Sn1—Cl1	87.39 (5)	C13—C8—C9	121.54 (16)
O1—Sn1—Cl1	163.16 (4)	O1—C9—C10	124.56 (17)
N1—Sn1—Cl1	88.85 (4)	O1—C9—C8	117.74 (16)
O1i—Sn1—Cl1	126.44 (3)	C10—C9—C8	117.69 (17)
C9—O1—Sn1	116.80 (11)	C9—C10—C11	120.93 (18)
C9—O1—Sn1i	132.84 (11)	C9—C10—H10	119.5
Sn1—O1—Sn1i	109.88 (5)	C11—C10—H10	119.5
C16—N1—C8	119.75 (17)	C12—C11—C10	121.63 (18)
C16—N1—Sn1	126.85 (13)	C12—C11—H11	119.2
C8—N1—Sn1	113.33 (12)	C10—C11—H11	119.2
Sn1—C1—H1A	109.5	C11—C12—C13	119.79 (18)
Sn1—C1—H1B	109.5	C11—C12—H12	120.1
H1A—C1—H1B	109.5	C13—C12—H12	120.1
Sn1—C1—H1C	109.5	C14—C13—C8	117.37 (17)
H1A—C1—H1C	109.5	C14—C13—C12	124.21 (18)
H1B—C1—H1C	109.5	C8—C13—C12	118.41 (17)
C3—C2—C7	118.50 (18)	C15—C14—C13	119.99 (18)
C3—C2—Sn1	121.01 (14)	C15—C14—H14	120.0
C7—C2—Sn1	120.46 (14)	C13—C14—H14	120.0
C2—C3—C4	120.78 (19)	C14—C15—C16	119.41 (18)
C2—C3—H3	119.6	C14—C15—H15	120.3
C4—C3—H3	119.6	C16—C15—H15	120.3
C5—C4—C3	120.03 (19)	N1—C16—C15	122.08 (17)
C5—C4—H4	120.0	N1—C16—H16	119.0
C3—C4—H4	120.0	C15—C16—H16	119.0
C1—Sn1—O1—C9	107.94 (13)	C3—C4—C5—C6	−1.1 (3)
C2—Sn1—O1—C9	−92.24 (13)	C4—C5—C6—C7	−0.2 (3)
N1—Sn1—O1—C9	6.53 (12)	C3—C2—C7—C6	−1.8 (3)
O1i—Sn1—O1—C9	−173.12 (15)	Sn1—C2—C7—C6	176.04 (14)
Cl1—Sn1—O1—C9	−2.8 (2)	C5—C6—C7—C2	1.7 (3)
C1—Sn1—O1—Sn1i	−78.95 (7)	C16—N1—C8—C13	0.7 (3)
C2—Sn1—O1—Sn1i	80.88 (7)	Sn1—N1—C8—C13	−176.16 (13)
N1—Sn1—O1—Sn1i	179.65 (7)	C16—N1—C8—C9	−178.36 (16)
O1i—Sn1—O1—Sn1i	0.0	Sn1—N1—C8—C9	4.7 (2)
Cl1—Sn1—O1—Sn1i	170.35 (8)	Sn1—O1—C9—C10	174.90 (14)
C1—Sn1—N1—C16	83.99 (16)	Sn1i—O1—C9—C10	3.7 (3)
C2—Sn1—N1—C16	−92.33 (16)	Sn1—O1—C9—C8	−6.4 (2)
O1—Sn1—N1—C16	177.53 (16)	Sn1i—O1—C9—C8	−177.52 (11)
O1i—Sn1—N1—C16	178.10 (13)	N1—C8—C9—O1	0.9 (2)
Cl1—Sn1—N1—C16	−5.16 (15)	C13—C8—C9—O1	−178.23 (16)
C1—Sn1—N1—C8	−99.37 (13)	N1—C8—C9—C10	179.70 (16)
C2—Sn1—N1—C8	84.31 (13)	C13—C8—C9—C10	0.6 (3)
O1—Sn1—N1—C8	−5.84 (12)	O1—C9—C10—C11	177.91 (17)
O1i—Sn1—N1—C8	−5.27 (17)	C8—C9—C10—C11	−0.8 (3)
Cl1—Sn1—N1—C8	171.48 (12)	C9—C10—C11—C12	0.3 (3)
C1—Sn1—C2—C3	−8.7 (3)	C10—C11—C12—C13	0.4 (3)
O1—Sn1—C2—C3	−123.54 (15)	N1—C8—C13—C14	0.0 (3)
N1—Sn1—C2—C3	161.73 (14)	C9—C8—C13—C14	179.06 (17)
O1i—Sn1—C2—C3	−53.99 (15)	N1—C8—C13—C12	−178.93 (16)
Cl1—Sn1—C2—C3	73.32 (14)	C9—C8—C13—C12	0.1 (3)
C1—Sn1—C2—C7	173.51 (16)	C11—C12—C13—C14	−179.50 (19)
O1—Sn1—C2—C7	58.69 (15)	C11—C12—C13—C8	−0.6 (3)
N1—Sn1—C2—C7	−16.04 (15)	C8—C13—C14—C15	−0.4 (3)
O1i—Sn1—C2—C7	128.23 (15)	C12—C13—C14—C15	178.46 (18)
Cl1—Sn1—C2—C7	−104.46 (14)	C13—C14—C15—C16	0.1 (3)
C7—C2—C3—C4	0.4 (3)	C8—N1—C16—C15	−1.1 (3)
Sn1—C2—C3—C4	−177.45 (14)	Sn1—N1—C16—C15	175.35 (13)
C2—C3—C4—C5	1.1 (3)	C14—C15—C16—N1	0.7 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl1ii	0.95	2.76	3.710 (2)	174

Symmetry codes: (ii) x−1, y, z.