Bis(μ-quinolin-8-olato)-κ3N,O:O;κ3O:N,O-bis­[chloridomethyl­phenyl­tin(IV)]

Vafaee, M.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536810027765

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m964

https://doi.org/10.1107/S1600536810027765

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Bis(μ-quinolin-8-olato)-κ³N,O:O;κ³O:N,O-bis[chloridomethylphenyltin(IV)]

Maryam Vafaee,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 July 2010; accepted 13 July 2010; online 17 July 2010)

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, P 2₁ /c
a = 7.9967 (5) Å
b = 17.8081 (10) Å
c = 10.1623 (6) Å
β = 95.232 (1)°
V = 1441.14 (15) Å³
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[F² > 2σ(F²)] = 0.018
wR(F²) = 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

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) x-1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027765/xu2799sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027765/xu2799Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

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.

Bis(µ-quinolin-8-olato)- κ³N,O:O;κ³O:N,O- bis[chloridomethylphenyltin(IV)] top

Crystal data top

[Sn₂(CH₃)₂(C₆H₅)₂(C₉H₆NO)₂Cl₂]	F(000) = 768
M_r = 780.84	D_x = 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 top

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

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.021P)² + 1.1915P] where P = (F_o² + 2F_c²)/3
3245 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Sn₂(CH₃)₂(C₆H₅)₂(C₉H₆NO)₂Cl₂]	V = 1441.14 (15) Å³
M_r = 780.84	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9967 (5) Å	µ = 1.95 mm⁻¹
b = 17.8081 (10) Å	T = 100 K
c = 10.1623 (6) Å	0.30 × 0.20 × 0.10 mm
β = 95.232 (1)°

Data collection top

Bruker SMART APEX diffractometer	3245 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3088 reflections with I > 2σ(I)
T_min = 0.592, T_max = 0.829	R_int = 0.017
9127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 1.09	Δρ_max = 0.43 e Å⁻³
3245 reflections	Δρ_min = −0.52 e Å⁻³
182 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Sn₂(CH₃)₂(C₆H₅)₂(C₉H₆NO)₂Cl₂]
M_r	780.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.9967 (5), 17.8081 (10), 10.1623 (6)
β (°)	95.232 (1)
V (Å³)	1441.14 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.95
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.592, 0.829
No. of measured, independent and observed [I > 2σ(I)] reflections	9127, 3245, 3088
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.047, 1.09
No. of reflections	3245
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.52

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

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