(Ethanol-κO)[2-(4-hydroxy­phen­yl)quinoline-4-carboxyl­ato-κO]triphenyl­tin(IV)

Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809012239

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m489

doi:10.1107/S1600536809012239

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(Ethanol-κO)[2-(4-hydroxyphenyl)quinoline-4-carboxylato-κO]triphenyltin(IV)

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 31 March 2009; accepted 1 April 2009; online 8 April 2009)

The Sn atom in the title molecule, [Sn(C₆H₅)₃(C₁₆H₁₀NO₃)(C₂H₆O)], shows a trans-C₃SnO₂ trigonal bipyramidal coordination. Adjacent molecules are linked by O—H⋯O and O—H⋯N hydrogen bonds into a two-dimensional array parallel to (100). The ethanol ligand is disordered, with two sites of equal occupancy being resolved for the ethyl group.

Related literature

Triphenyltin carboxylates are coordinately saturated, and do not generally afford adducts; for some unusual examples of adducts with oxygen-donor ligands, see: Ng & Kumar Das (1997 ). For reviews of the structural chemistry of organotin carboxylates, see: Tiekink (1991 , 1994 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₁₆H₁₀NO₃)(C₂H₆O)]
M_r = 660.31
Monoclinic, C 2/c
a = 38.9542 (5) Å
b = 9.7259 (2) Å
c = 17.8594 (3) Å
β = 116.632 (1)°
V = 6048.4 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.89 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 = 0.777, T_max = 0.917
23944 measured reflections
6937 independent reflections
5517 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.104
S = 1.26
6937 reflections
395 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.21 e Å⁻³
Δρ_min = −1.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.85 (1)	1.83 (2)	2.661 (3)	166 (6)
O4—H4⋯N1ⁱⁱ	0.84 (1)	1.95 (1)	2.789 (4)	175 (4)
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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: publlCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012239/tk2412sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012239/tk2412Isup2.hkl

checkCIF report

Related literature top

Triphenyltin carboxylates are coordinately saturated, and do not generally afford adducts; for some unusual examples of adducts with oxygen-donor ligands, see: Ng & Kumar Das (1997). For reviews of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Re-distilled benzaldehyde (12 ml) and pyruvic acid (11 g) were boiled in ethanol (100 ml) and to the solution was added 4-hydroxyaniline (11.5 ml). The mixture was heated for another 3 h. The solution was cooled and the solid product recrystallized from ethanol to give yellow 2-(4-hydroxyphenyl)quinoline-4-carboxylic acid.

Triphenyltin hydroxide (0.37 g, 1 mmol) and 2-(4-hydroxyphenyl)quinoline-4-carboxylic acid (0.27 g, 1 mol) were heated in ethanol (25 mol) until the reactants dissolved completely. The solution was filtered and the solvent allowed to evaporate slowly. Crystals were deposited after several days.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. 70% Probability thermal ellipsoid plot (Barbour, 2001) of Sn(C₆H₅)₃(C₂H₆O)(C₁₅H₁₀NO). Hydrogen atoms are drawn as spheres of arbitrary radii. The disorder in the ethanol molecule is not shown.

(Ethanol-κO)[2-(4-hydroxyphenyl)quinoline-4-carboxylato- κO]triphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃(C₁₆H₁₀NO₃)(C₂H₆O)]	F(000) = 2688
M_r = 660.31	D_x = 1.450 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7502 reflections
a = 38.9542 (5) Å	θ = 2.3–27.9°
b = 9.7259 (2) Å	µ = 0.89 mm⁻¹
c = 17.8594 (3) Å	T = 100 K
β = 116.632 (1)°	Irregular block, yellow
V = 6048.4 (2) Å³	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	6937 independent reflections
Radiation source: fine-focus sealed tube	5517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.5°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −50→50
T_min = 0.777, T_max = 0.917	k = −12→12
23944 measured reflections	l = −22→23

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
6937 reflections	(Δ/σ)_max = 0.001
395 parameters	Δρ_max = 1.21 e Å⁻³
19 restraints	Δρ_min = −1.30 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₁₆H₁₀NO₃)(C₂H₆O)]	V = 6048.4 (2) Å³
M_r = 660.31	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 38.9542 (5) Å	µ = 0.89 mm⁻¹
b = 9.7259 (2) Å	T = 100 K
c = 17.8594 (3) Å	0.30 × 0.20 × 0.10 mm
β = 116.632 (1)°

Data collection top

Bruker SMART APEX diffractometer	6937 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5517 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.917	R_int = 0.038
23944 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	19 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	Δρ_max = 1.21 e Å⁻³
6937 reflections	Δρ_min = −1.30 e Å⁻³
395 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.644792 (5)	0.66381 (2)	0.651964 (13)	0.01976 (8)
O1	0.64978 (6)	0.4794 (2)	0.72684 (13)	0.0230 (5)
O2	0.58946 (6)	0.4207 (2)	0.64055 (13)	0.0259 (5)
O3	0.46240 (7)	0.2226 (3)	0.92855 (17)	0.0363 (6)
H3	0.4486 (14)	0.294 (4)	0.913 (4)	0.09 (2)*
O4	0.63966 (7)	0.8677 (2)	0.57574 (15)	0.0275 (5)
H4	0.6351 (11)	0.861 (4)	0.5250 (10)	0.040 (12)*
N1	0.61942 (7)	0.1541 (3)	0.90533 (16)	0.0210 (5)
C1	0.59940 (9)	0.7431 (3)	0.6739 (2)	0.0257 (7)
C2	0.56082 (9)	0.7165 (4)	0.6215 (2)	0.0314 (8)
H2	0.5539	0.6600	0.5735	0.038*
C3	0.53252 (10)	0.7721 (5)	0.6392 (3)	0.0429 (10)
H3A	0.5062	0.7548	0.6028	0.051*
C4	0.54256 (12)	0.8532 (4)	0.7101 (3)	0.0466 (11)
H4A	0.5231	0.8899	0.7224	0.056*
C5	0.58029 (11)	0.8807 (4)	0.7621 (2)	0.0414 (9)
H5	0.5869	0.9370	0.8101	0.050*
C6	0.60898 (10)	0.8257 (4)	0.7446 (2)	0.0324 (8)
H6	0.6352	0.8445	0.7809	0.039*
C7	0.70093 (8)	0.7263 (3)	0.74125 (19)	0.0210 (6)
C8	0.71841 (9)	0.6630 (3)	0.8197 (2)	0.0254 (7)
H8	0.7049	0.5944	0.8337	0.030*
C9	0.75550 (10)	0.6996 (4)	0.8775 (2)	0.0329 (8)
H9	0.7670	0.6560	0.9308	0.040*
C10	0.77560 (9)	0.7981 (4)	0.8582 (2)	0.0321 (8)
H10	0.8009	0.8222	0.8977	0.038*
C11	0.75878 (10)	0.8613 (4)	0.7815 (2)	0.0310 (8)
H11	0.7726	0.9292	0.7679	0.037*
C12	0.72155 (9)	0.8269 (3)	0.7230 (2)	0.0275 (7)
H12	0.7102	0.8724	0.6704	0.033*
C13	0.64468 (9)	0.5595 (3)	0.54688 (19)	0.0218 (6)
C14	0.61920 (9)	0.4569 (4)	0.5032 (2)	0.0289 (7)
H14	0.5990	0.4338	0.5170	0.035*
C15	0.62271 (11)	0.3867 (4)	0.4391 (2)	0.0372 (8)
H15	0.6048	0.3167	0.4090	0.045*
C16	0.65208 (10)	0.4186 (4)	0.4192 (2)	0.0360 (8)
H16	0.6547	0.3696	0.3761	0.043*
C17	0.67774 (10)	0.5222 (4)	0.4621 (2)	0.0308 (8)
H17	0.6978	0.5452	0.4480	0.037*
C18	0.67411 (9)	0.5921 (3)	0.5256 (2)	0.0253 (7)
H18	0.6918	0.6630	0.5550	0.030*
C19	0.61924 (8)	0.4091 (3)	0.70774 (19)	0.0207 (6)
C20	0.62011 (8)	0.3120 (3)	0.77441 (19)	0.0208 (6)
C21	0.65106 (8)	0.2215 (3)	0.81930 (19)	0.0201 (6)
C22	0.68306 (9)	0.2038 (3)	0.8023 (2)	0.0245 (7)
H22	0.6847	0.2558	0.7589	0.029*
C23	0.71155 (9)	0.1129 (4)	0.8476 (2)	0.0297 (7)
H23	0.7328	0.1021	0.8355	0.036*
C24	0.70965 (10)	0.0351 (4)	0.9119 (2)	0.0329 (8)
H24	0.7296	−0.0282	0.9429	0.039*
C25	0.67905 (9)	0.0498 (4)	0.9305 (2)	0.0300 (7)
H25	0.6781	−0.0028	0.9743	0.036*
C26	0.64924 (8)	0.1431 (3)	0.8845 (2)	0.0222 (7)
C27	0.59012 (8)	0.2362 (3)	0.85988 (19)	0.0203 (6)
C28	0.58973 (8)	0.3161 (3)	0.79347 (19)	0.0218 (6)
H28	0.5683	0.3731	0.7618	0.026*
C29	0.55701 (8)	0.2372 (3)	0.87918 (19)	0.0206 (6)
C30	0.54731 (9)	0.1182 (3)	0.9091 (2)	0.0242 (7)
H30	0.5627	0.0382	0.9189	0.029*
C31	0.51552 (9)	0.1148 (4)	0.9249 (2)	0.0273 (7)
H31	0.5091	0.0327	0.9445	0.033*
C32	0.49321 (9)	0.2316 (4)	0.9118 (2)	0.0262 (7)
C33	0.50289 (9)	0.3521 (3)	0.8844 (2)	0.0254 (7)
H33	0.4881	0.4329	0.8772	0.030*
C34	0.53440 (8)	0.3541 (3)	0.8673 (2)	0.0236 (7)
H34	0.5406	0.4363	0.8472	0.028*
C35	0.6218 (2)	0.9877 (7)	0.5981 (5)	0.0383 (12)	0.50
H35A	0.6321	0.9950	0.6597	0.046*	0.50
H35B	0.5936	0.9756	0.5736	0.046*	0.50
C36	0.6315 (2)	1.1177 (6)	0.5627 (5)	0.0383 (12)	0.50
H36A	0.6593	1.1214	0.5809	0.057*	0.50
H36B	0.6236	1.1992	0.5832	0.057*	0.50
H36C	0.6180	1.1155	0.5014	0.057*	0.50
C35'	0.6461 (3)	1.0012 (8)	0.6165 (8)	0.084 (3)	0.50
H35C	0.6616	1.0586	0.5973	0.101*	0.50
H35D	0.6610	0.9883	0.6778	0.101*	0.50
C36'	0.6073 (3)	1.0809 (9)	0.5981 (8)	0.084 (3)	0.50
H36D	0.5961	1.1184	0.5412	0.126*	0.50
H36E	0.6128	1.1561	0.6384	0.126*	0.50
H36F	0.5890	1.0170	0.6034	0.126*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01769 (11)	0.02596 (12)	0.01585 (12)	0.00055 (8)	0.00772 (9)	−0.00158 (9)
O1	0.0202 (10)	0.0300 (12)	0.0210 (11)	−0.0031 (9)	0.0112 (9)	0.0010 (9)
O2	0.0216 (11)	0.0377 (13)	0.0186 (12)	−0.0011 (10)	0.0090 (9)	0.0034 (10)
O3	0.0231 (12)	0.0563 (17)	0.0374 (15)	0.0086 (12)	0.0206 (11)	0.0141 (13)
O4	0.0355 (13)	0.0270 (12)	0.0168 (12)	0.0026 (10)	0.0088 (10)	−0.0001 (10)
N1	0.0198 (12)	0.0272 (14)	0.0177 (13)	0.0009 (10)	0.0098 (11)	0.0007 (11)
C1	0.0254 (16)	0.0329 (18)	0.0207 (17)	0.0053 (13)	0.0120 (13)	0.0011 (14)
C2	0.0283 (17)	0.0400 (19)	0.0254 (19)	0.0053 (15)	0.0116 (15)	−0.0015 (16)
C3	0.0260 (18)	0.063 (3)	0.039 (2)	0.0108 (18)	0.0136 (17)	0.002 (2)
C4	0.040 (2)	0.064 (3)	0.046 (3)	0.0192 (19)	0.029 (2)	0.001 (2)
C5	0.047 (2)	0.049 (2)	0.032 (2)	0.0128 (19)	0.0218 (18)	−0.0069 (18)
C6	0.0304 (17)	0.040 (2)	0.0262 (19)	0.0037 (15)	0.0122 (15)	−0.0052 (16)
C7	0.0182 (14)	0.0276 (16)	0.0181 (16)	−0.0013 (12)	0.0090 (12)	−0.0032 (13)
C8	0.0236 (15)	0.0324 (17)	0.0217 (17)	−0.0029 (13)	0.0115 (13)	0.0029 (14)
C9	0.0264 (17)	0.044 (2)	0.0235 (19)	−0.0006 (15)	0.0063 (14)	0.0029 (16)
C10	0.0207 (15)	0.0377 (19)	0.035 (2)	−0.0045 (14)	0.0094 (15)	−0.0077 (16)
C11	0.0264 (17)	0.0342 (19)	0.037 (2)	−0.0086 (14)	0.0182 (16)	−0.0053 (16)
C12	0.0286 (16)	0.0325 (18)	0.0212 (17)	−0.0011 (14)	0.0110 (14)	0.0020 (14)
C13	0.0220 (14)	0.0271 (16)	0.0169 (15)	0.0054 (12)	0.0092 (12)	0.0024 (13)
C14	0.0293 (17)	0.0385 (19)	0.0226 (18)	−0.0019 (14)	0.0151 (14)	−0.0039 (15)
C15	0.038 (2)	0.047 (2)	0.027 (2)	−0.0056 (17)	0.0145 (16)	−0.0123 (17)
C16	0.042 (2)	0.049 (2)	0.0227 (19)	0.0059 (17)	0.0189 (16)	−0.0024 (17)
C17	0.0330 (17)	0.040 (2)	0.0254 (18)	0.0068 (15)	0.0185 (15)	0.0036 (15)
C18	0.0246 (15)	0.0306 (18)	0.0215 (17)	0.0019 (13)	0.0109 (13)	0.0026 (14)
C19	0.0200 (14)	0.0265 (16)	0.0186 (16)	0.0007 (12)	0.0115 (13)	−0.0006 (13)
C20	0.0187 (14)	0.0267 (16)	0.0165 (15)	−0.0056 (12)	0.0074 (12)	−0.0031 (12)
C21	0.0192 (14)	0.0249 (15)	0.0163 (15)	−0.0022 (12)	0.0082 (12)	−0.0016 (13)
C22	0.0242 (15)	0.0318 (17)	0.0212 (17)	0.0004 (13)	0.0136 (13)	−0.0016 (14)
C23	0.0247 (16)	0.0375 (18)	0.033 (2)	0.0010 (15)	0.0178 (15)	0.0002 (16)
C24	0.0271 (17)	0.040 (2)	0.032 (2)	0.0123 (15)	0.0131 (15)	0.0077 (16)
C25	0.0257 (16)	0.0387 (19)	0.0271 (18)	0.0065 (14)	0.0133 (14)	0.0069 (15)
C26	0.0168 (14)	0.0279 (17)	0.0219 (17)	−0.0029 (12)	0.0086 (12)	−0.0022 (13)
C27	0.0172 (14)	0.0249 (16)	0.0187 (16)	−0.0022 (12)	0.0080 (12)	−0.0009 (13)
C28	0.0161 (13)	0.0300 (17)	0.0172 (15)	−0.0005 (12)	0.0054 (12)	0.0015 (13)
C29	0.0161 (13)	0.0304 (17)	0.0168 (15)	−0.0012 (12)	0.0085 (12)	0.0009 (13)
C30	0.0233 (15)	0.0269 (16)	0.0244 (17)	0.0030 (13)	0.0125 (14)	0.0022 (14)
C31	0.0236 (16)	0.0345 (17)	0.0248 (18)	−0.0011 (14)	0.0118 (14)	0.0056 (15)
C32	0.0194 (15)	0.0396 (19)	0.0207 (17)	0.0014 (14)	0.0100 (13)	0.0022 (15)
C33	0.0192 (14)	0.0347 (18)	0.0215 (17)	0.0061 (13)	0.0085 (13)	0.0035 (14)
C34	0.0201 (14)	0.0311 (17)	0.0189 (16)	0.0018 (13)	0.0081 (13)	0.0045 (13)
C35	0.035 (3)	0.040 (3)	0.036 (3)	−0.003 (2)	0.013 (2)	−0.002 (2)
C36	0.035 (3)	0.040 (3)	0.036 (3)	−0.003 (2)	0.013 (2)	−0.002 (2)
C35'	0.065 (5)	0.032 (3)	0.109 (6)	0.013 (3)	−0.001 (4)	−0.012 (4)
C36'	0.065 (5)	0.032 (3)	0.109 (6)	0.013 (3)	−0.001 (4)	−0.012 (4)

Geometric parameters (Å, º) top

Sn1—C1	2.120 (3)	C16—H16	0.9500
Sn1—C13	2.131 (3)	C17—C18	1.382 (4)
Sn1—C7	2.138 (3)	C17—H17	0.9500
Sn1—O1	2.193 (2)	C18—H18	0.9500
Sn1—O4	2.363 (2)	C19—C20	1.509 (4)
O1—C19	1.279 (3)	C20—C28	1.371 (4)
O2—C19	1.245 (4)	C20—C21	1.416 (4)
O3—C32	1.363 (4)	C21—C26	1.419 (4)
O3—H3	0.846 (10)	C21—C22	1.420 (4)
O4—C35'	1.454 (7)	C22—C23	1.365 (5)
O4—C35	1.502 (6)	C22—H22	0.9500
O4—H4	0.844 (10)	C23—C24	1.405 (5)
N1—C27	1.330 (4)	C23—H23	0.9500
N1—C26	1.374 (4)	C24—C25	1.380 (4)
C1—C2	1.393 (5)	C24—H24	0.9500
C1—C6	1.399 (5)	C25—C26	1.411 (4)
C2—C3	1.386 (5)	C25—H25	0.9500
C2—H2	0.9500	C27—C28	1.412 (4)
C3—C4	1.391 (6)	C27—C29	1.477 (4)
C3—H3A	0.9500	C28—H28	0.9500
C4—C5	1.368 (6)	C29—C34	1.395 (4)
C4—H4A	0.9500	C29—C30	1.396 (4)
C5—C6	1.396 (5)	C30—C31	1.387 (4)
C5—H5	0.9500	C30—H30	0.9500
C6—H6	0.9500	C31—C32	1.385 (5)
C7—C12	1.393 (4)	C31—H31	0.9500
C7—C8	1.396 (4)	C32—C33	1.386 (5)
C8—C9	1.394 (5)	C33—C34	1.391 (4)
C8—H8	0.9500	C33—H33	0.9500
C9—C10	1.376 (5)	C34—H34	0.9500
C9—H9	0.9500	C35—C36	1.537 (7)
C10—C11	1.371 (5)	C35—H35A	0.9900
C10—H10	0.9500	C35—H35B	0.9900
C11—C12	1.396 (5)	C36—H36A	0.9800
C11—H11	0.9500	C36—H36B	0.9800
C12—H12	0.9500	C36—H36C	0.9800
C13—C14	1.377 (5)	C35'—C36'	1.595 (13)
C13—C18	1.397 (4)	C35'—H35C	0.9900
C14—C15	1.391 (5)	C35'—H35D	0.9900
C14—H14	0.9500	C36'—H36D	0.9800
C15—C16	1.377 (5)	C36'—H36E	0.9800
C15—H15	0.9500	C36'—H36F	0.9800
C16—C17	1.384 (5)

C1—Sn1—C13	131.51 (12)	C17—C18—C13	120.7 (3)
C1—Sn1—C7	114.71 (12)	C17—C18—H18	119.7
C13—Sn1—C7	112.95 (11)	C13—C18—H18	119.7
C1—Sn1—O1	92.20 (10)	O2—C19—O1	124.2 (3)
C13—Sn1—O1	96.45 (10)	O2—C19—C20	119.9 (3)
C7—Sn1—O1	89.79 (10)	O1—C19—C20	115.8 (3)
C1—Sn1—O4	86.49 (11)	C28—C20—C21	119.2 (3)
C13—Sn1—O4	85.76 (10)	C28—C20—C19	117.5 (3)
C7—Sn1—O4	89.14 (10)	C21—C20—C19	123.3 (3)
O1—Sn1—O4	177.78 (8)	C20—C21—C26	117.1 (3)
C19—O1—Sn1	117.18 (19)	C20—C21—C22	124.1 (3)
C32—O3—H3	111 (4)	C26—C21—C22	118.8 (3)
C35'—O4—Sn1	120.6 (6)	C23—C22—C21	120.7 (3)
C35—O4—Sn1	115.3 (3)	C23—C22—H22	119.7
C35'—O4—H4	121 (3)	C21—C22—H22	119.7
C35—O4—H4	116 (3)	C22—C23—C24	120.4 (3)
Sn1—O4—H4	119 (3)	C22—C23—H23	119.8
C27—N1—C26	118.7 (3)	C24—C23—H23	119.8
C2—C1—C6	118.9 (3)	C25—C24—C23	120.6 (3)
C2—C1—Sn1	123.1 (2)	C25—C24—H24	119.7
C6—C1—Sn1	117.9 (2)	C23—C24—H24	119.7
C3—C2—C1	120.2 (3)	C24—C25—C26	120.0 (3)
C3—C2—H2	119.9	C24—C25—H25	120.0
C1—C2—H2	119.9	C26—C25—H25	120.0
C2—C3—C4	120.1 (4)	N1—C26—C25	117.8 (3)
C2—C3—H3A	120.0	N1—C26—C21	122.7 (3)
C4—C3—H3A	120.0	C25—C26—C21	119.5 (3)
C5—C4—C3	120.5 (3)	N1—C27—C28	121.7 (3)
C5—C4—H4A	119.7	N1—C27—C29	117.5 (3)
C3—C4—H4A	119.7	C28—C27—C29	120.7 (3)
C4—C5—C6	119.8 (4)	C20—C28—C27	120.5 (3)
C4—C5—H5	120.1	C20—C28—H28	119.8
C6—C5—H5	120.1	C27—C28—H28	119.8
C5—C6—C1	120.4 (3)	C34—C29—C30	118.2 (3)
C5—C6—H6	119.8	C34—C29—C27	121.9 (3)
C1—C6—H6	119.8	C30—C29—C27	119.9 (3)
C12—C7—C8	118.1 (3)	C31—C30—C29	121.1 (3)
C12—C7—Sn1	122.0 (2)	C31—C30—H30	119.4
C8—C7—Sn1	119.9 (2)	C29—C30—H30	119.4
C9—C8—C7	120.6 (3)	C32—C31—C30	119.7 (3)
C9—C8—H8	119.7	C32—C31—H31	120.1
C7—C8—H8	119.7	C30—C31—H31	120.1
C10—C9—C8	120.6 (3)	O3—C32—C31	117.3 (3)
C10—C9—H9	119.7	O3—C32—C33	122.5 (3)
C8—C9—H9	119.7	C31—C32—C33	120.2 (3)
C11—C10—C9	119.5 (3)	C32—C33—C34	119.8 (3)
C11—C10—H10	120.3	C32—C33—H33	120.1
C9—C10—H10	120.3	C34—C33—H33	120.1
C10—C11—C12	120.7 (3)	C33—C34—C29	120.9 (3)
C10—C11—H11	119.6	C33—C34—H34	119.5
C12—C11—H11	119.6	C29—C34—H34	119.5
C7—C12—C11	120.5 (3)	O4—C35—C36	107.4 (5)
C7—C12—H12	119.7	O4—C35—H35A	110.2
C11—C12—H12	119.7	C36—C35—H35A	110.2
C14—C13—C18	118.8 (3)	O4—C35—H35B	110.2
C14—C13—Sn1	124.1 (2)	C36—C35—H35B	110.2
C18—C13—Sn1	117.0 (2)	H35A—C35—H35B	108.5
C13—C14—C15	120.7 (3)	O4—C35'—C36'	113.3 (8)
C13—C14—H14	119.7	O4—C35'—H35C	108.9
C15—C14—H14	119.7	C36'—C35'—H35C	108.9
C16—C15—C14	120.1 (3)	O4—C35'—H35D	108.9
C16—C15—H15	119.9	C36'—C35'—H35D	108.9
C14—C15—H15	119.9	H35C—C35'—H35D	107.7
C15—C16—C17	119.9 (3)	C35'—C36'—H36D	109.5
C15—C16—H16	120.1	C35'—C36'—H36E	109.5
C17—C16—H16	120.1	H36D—C36'—H36E	109.5
C18—C17—C16	119.9 (3)	C35'—C36'—H36F	109.5
C18—C17—H17	120.0	H36D—C36'—H36F	109.5
C16—C17—H17	120.0	H36E—C36'—H36F	109.5

C1—Sn1—O1—C19	53.6 (2)	C14—C15—C16—C17	−1.1 (6)
C13—Sn1—O1—C19	−78.6 (2)	C15—C16—C17—C18	0.9 (5)
C7—Sn1—O1—C19	168.4 (2)	C16—C17—C18—C13	−0.2 (5)
C1—Sn1—O4—C35'	61.0 (6)	C14—C13—C18—C17	−0.3 (5)
C13—Sn1—O4—C35'	−166.9 (6)	Sn1—C13—C18—C17	175.4 (2)
C7—Sn1—O4—C35'	−53.8 (6)	Sn1—O1—C19—O2	15.7 (4)
C1—Sn1—O4—C35	23.0 (4)	Sn1—O1—C19—C20	−161.42 (19)
C13—Sn1—O4—C35	155.1 (4)	O2—C19—C20—C28	−46.6 (4)
C7—Sn1—O4—C35	−91.8 (4)	O1—C19—C20—C28	130.7 (3)
C13—Sn1—C1—C2	9.9 (4)	O2—C19—C20—C21	135.5 (3)
C7—Sn1—C1—C2	178.5 (3)	O1—C19—C20—C21	−47.2 (4)
O1—Sn1—C1—C2	−90.7 (3)	C28—C20—C21—C26	−2.3 (4)
O4—Sn1—C1—C2	91.1 (3)	C19—C20—C21—C26	175.5 (3)
C13—Sn1—C1—C6	−170.3 (2)	C28—C20—C21—C22	176.8 (3)
C7—Sn1—C1—C6	−1.7 (3)	C19—C20—C21—C22	−5.3 (5)
O1—Sn1—C1—C6	89.1 (3)	C20—C21—C22—C23	−179.0 (3)
O4—Sn1—C1—C6	−89.1 (3)	C26—C21—C22—C23	0.1 (5)
C6—C1—C2—C3	0.5 (5)	C21—C22—C23—C24	0.0 (5)
Sn1—C1—C2—C3	−179.7 (3)	C22—C23—C24—C25	−0.3 (6)
C1—C2—C3—C4	−0.9 (6)	C23—C24—C25—C26	0.3 (5)
C2—C3—C4—C5	1.0 (7)	C27—N1—C26—C25	−176.6 (3)
C3—C4—C5—C6	−0.7 (7)	C27—N1—C26—C21	3.5 (4)
C4—C5—C6—C1	0.2 (6)	C24—C25—C26—N1	180.0 (3)
C2—C1—C6—C5	−0.1 (5)	C24—C25—C26—C21	−0.2 (5)
Sn1—C1—C6—C5	−180.0 (3)	C20—C21—C26—N1	−1.0 (4)
C1—Sn1—C7—C12	−103.7 (3)	C22—C21—C26—N1	179.8 (3)
C13—Sn1—C7—C12	67.1 (3)	C20—C21—C26—C25	179.1 (3)
O1—Sn1—C7—C12	164.0 (3)	C22—C21—C26—C25	−0.1 (5)
O4—Sn1—C7—C12	−17.9 (3)	C26—N1—C27—C28	−2.7 (4)
C1—Sn1—C7—C8	78.2 (3)	C26—N1—C27—C29	175.0 (3)
C13—Sn1—C7—C8	−111.0 (3)	C21—C20—C28—C27	3.2 (5)
O1—Sn1—C7—C8	−14.1 (2)	C19—C20—C28—C27	−174.8 (3)
O4—Sn1—C7—C8	163.9 (3)	N1—C27—C28—C20	−0.7 (5)
C12—C7—C8—C9	−0.3 (5)	C29—C27—C28—C20	−178.3 (3)
Sn1—C7—C8—C9	177.9 (3)	N1—C27—C29—C34	149.5 (3)
C7—C8—C9—C10	−0.3 (5)	C28—C27—C29—C34	−32.8 (4)
C8—C9—C10—C11	0.4 (5)	N1—C27—C29—C30	−31.4 (4)
C9—C10—C11—C12	0.2 (5)	C28—C27—C29—C30	146.3 (3)
C8—C7—C12—C11	0.9 (5)	C34—C29—C30—C31	1.5 (5)
Sn1—C7—C12—C11	−177.3 (2)	C27—C29—C30—C31	−177.6 (3)
C10—C11—C12—C7	−0.8 (5)	C29—C30—C31—C32	−0.9 (5)
C1—Sn1—C13—C14	−43.2 (3)	C30—C31—C32—O3	−179.8 (3)
C7—Sn1—C13—C14	148.0 (3)	C30—C31—C32—C33	−0.9 (5)
O1—Sn1—C13—C14	55.5 (3)	O3—C32—C33—C34	−179.1 (3)
O4—Sn1—C13—C14	−124.7 (3)	C31—C32—C33—C34	2.1 (5)
C1—Sn1—C13—C18	141.4 (2)	C32—C33—C34—C29	−1.4 (5)
C7—Sn1—C13—C18	−27.4 (3)	C30—C29—C34—C33	−0.3 (5)
O1—Sn1—C13—C18	−119.9 (2)	C27—C29—C34—C33	178.8 (3)
O4—Sn1—C13—C18	59.9 (2)	C35'—O4—C35—C36	55.8 (11)
C18—C13—C14—C15	0.1 (5)	Sn1—O4—C35—C36	163.7 (4)
Sn1—C13—C14—C15	−175.3 (3)	C35—O4—C35'—C36'	−10.5 (8)
C13—C14—C15—C16	0.6 (6)	Sn1—O4—C35'—C36'	−101.1 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.85 (1)	1.83 (2)	2.661 (3)	166 (6)
O4—H4···N1ⁱⁱ	0.84 (1)	1.95 (1)	2.789 (4)	175 (4)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₁₆H₁₀NO₃)(C₂H₆O)]
M_r	660.31
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	38.9542 (5), 9.7259 (2), 17.8594 (3)
β (°)	116.632 (1)
V (Å³)	6048.4 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
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	0.777, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	23944, 6937, 5517
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.104, 1.26
No. of reflections	6937
No. of parameters	395
No. of restraints	19
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.21, −1.30

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.85 (1)	1.83 (2)	2.661 (3)	166 (6)
O4—H4···N1ⁱⁱ	0.84 (1)	1.95 (1)	2.789 (4)	175 (4)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, −y+1, z−1/2.

Acknowledgements

We thank the University of Malaya (FS3392008A) for funding this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ng, S. W. & Kumar Das, V. G. (1997). Trends Organomet. Chem. 2, 107–115. CAS 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
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23. CrossRef CAS Web of Science Google Scholar
Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71–116. Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 65| Part 5| May 2009| Page m489

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

(Ethanol-κO)[2-(4-hy­droxy­phen­yl)quinoline-4-carboxyl­ato-κO]tri­phenyl­tin(IV)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(Ethanol-κO)[2-(4-hydroxyphenyl)quinoline-4-carboxylato-κO]triphenyltin(IV)