catena-Poly[[triphenyl­tin(IV)]-μ2-[3-(cyclo­hexyl­carbamo­yl)propanoato-κ2O1:O3]]

Shams-ul-Islam, S.; Bhatti, M.H.; Imtiaz-ud-Din; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536810036500

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1266-m1267

doi:10.1107/S1600536810036500

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catena-Poly[[triphenyltin(IV)]-μ₂-[3-(cyclohexylcarbamoyl)propanoato-κ²O¹:O³]]

S. Shams-ul-Islam,^a Moazzam H. Bhatti,^a Imtiaz-ud-Din,^a Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Allama Iqbal Open University, Islamabad 44000, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 September 2010; accepted 13 September 2010; online 18 September 2010)

The Sn atom in the polymeric title compound, [Sn(C₆H₅)₃(C₁₀H₁₆NO₃)]_n, is five-coordinated within a trans-C₃O₂ donor set that defines an approximate trigonal-bipyramidal geometry. The carboxylate ligand is monodentate and the amide O atom bridges a symmetry-related Sn atom, generating a chain along [010] with a linear topology. An intramolecular carboxylate–carbonyl N—H⋯O hydrogen bond is responsible for the curved conformation within the carboxylate ligand.

Related literature

For reviews of organotin carboxylate structures, see: Ng et al. (1986 ); Tiekink (1991 ). For the influence of steric effects upon structural motifs, see: Willem et al. (1998 ). For a closely related structure, see: Imtiaz-ud-Din et al. (2010 ). For additional geometric analysis, see: Addison et al. (1984 ). For the synthesis of N-cyclohexylsuccinamic acid, see: Dolzhenko et al. (2003 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₁₀H₁₆NO₃)]
M_r = 548.23
Monoclinic, P 2₁ /c
a = 16.2488 (12) Å
b = 9.1243 (7) Å
c = 17.6597 (13) Å
β = 106.101 (1)°
V = 2515.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.634, T_max = 0.746
23281 measured reflections
5756 independent reflections
4864 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.084
S = 1.03
5756 reflections
302 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn—O1	2.1658 (17)
Sn—O3ⁱ	2.3178 (16)
Sn—C1	2.138 (2)
Sn—C7	2.129 (3)
Sn—C13	2.130 (3)
Symmetry code: (i) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86 (1)	1.93 (2)	2.732 (3)	155 (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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036500/hg2713sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036500/hg2713Isup2.hkl

checkCIF report

Comment top

Triorganotin carboxylates are usually monomeric or polymeric (Ng et al., 1986; Tiekink, 1991), depending largely on steric factors (Willem et al., 1998). As a continuation of recent studies on triorganotin carboxylates having carboxylate ligands with additional coordination functionality (Imtiaz-ud-Din et al., 2010), the title compound, (I), was investigated.

In (I), Fig. 1, the Sn atom is coordinated by three ipso-C atoms derived from three phenyl groups, an O atom from a monodentate carboxylate ligand, and, from a symmetry related molecule, an amide-O atom, to define a trans-C₃O₂ coordination geometry, Table 1. The value of τ computes to 0.73 compared to τ = 1.0 for an ideal trigonal bipyramid and τ = 0.0 for an ideal square pyramid (Addison et al., 1984). The distortion in the Sn atom geometry is ascribed, in part, to the close approach of the O2 atom; Sn···O2 = 2.9936 (17) Å. The central part of the carboxylate ligand is curved, e.g. the C19–C20–C21–C22 torsion angle = -77.3 (3) °, owing to the presence of an intramolecular N–H···O2 hydrogen bond, Table 2. The resulting supramolecular chain has a linear topology, Fig. 2, in contrast to the helical chain found recently in the structure of the benzoate derivative (Imtiaz-ud-Din et al., 2010).

Related literature top

For reviews of organotin carboxylate structures, see: Ng et al. (1986); Tiekink (1991). For the influence of steric effects upon structural motifs, see: Willem et al. (1998). For a closely related structure, see: Imtiaz-ud-Din et al. (2010). For additional geometric analysis, see: Addison et al. (1984). For the synthesis of N-cyclohexylsuccinamic acid, see: Dolzhenko et al. (2003).

Experimental top

N-Cyclohexylsuccinamic acid was synthesized from the reaction of succinic anhydride and cyclohexylamine in ethyl acetate by the methodology reported earlier (Dolzhenko et al., 2003). Triphenyltin hydroxide (3.17 g, 10 mmol) and N-cyclohexylsuccinamic acid (2.66 g, 10 mmol) were heated to reflux in 50 ml dry ethanol/acetone mixture (8:2) for 6–8 h, The solvent was then removed under reduced pressure and the solid mass thus obtained was recrystallized from a mixture of chloroform and n-hexane (3:1) to furnish colourless crystals.

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the asymmetric unit in (I) extended to show the bridging atoms and showing the atom-labelling scheme with displacement ellipsoids at the 50% probability level. Symmetry operation i: x, 1 + y, z; ii: x, -1 + y, z.
	Fig. 2. A portion of the linear polymeric chain in (I). Colour code: Sn, orange; O, red; N, blue; C, grey; H, green.

catena-Poly[[triphenyltin(IV)]-µ₂-[3-(cyclohexylcarbamoyl)propanoato- κ²O¹:O³]] top

Crystal data top

[Sn(C₆H₅)₃(C₁₀H₁₆NO₃)]	F(000) = 1120
M_r = 548.23	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5969 reflections
a = 16.2488 (12) Å	θ = 2.4–28.2°
b = 9.1243 (7) Å	µ = 1.04 mm⁻¹
c = 17.6597 (13) Å	T = 100 K
β = 106.101 (1)°	Block, colourless
V = 2515.5 (3) Å³	0.25 × 0.15 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5756 independent reflections
Radiation source: fine-focus sealed tube	4864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scan	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.634, T_max = 0.746	k = −11→11
23281 measured reflections	l = −22→22

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
5756 reflections	(Δ/σ)_max = 0.002
302 parameters	Δρ_max = 0.53 e Å⁻³
1 restraint	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₁₀H₁₆NO₃)]	V = 2515.5 (3) Å³
M_r = 548.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.2488 (12) Å	µ = 1.04 mm⁻¹
b = 9.1243 (7) Å	T = 100 K
c = 17.6597 (13) Å	0.25 × 0.15 × 0.05 mm
β = 106.101 (1)°

Data collection top

Bruker SMART APEX diffractometer	5756 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4864 reflections with I > 2σ(I)
T_min = 0.634, T_max = 0.746	R_int = 0.047
23281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.53 e Å⁻³
5756 reflections	Δρ_min = −0.64 e Å⁻³
302 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
Sn	0.713719 (10)	0.684277 (17)	0.636309 (10)	0.01166 (7)
O1	0.69004 (11)	0.47709 (18)	0.57420 (10)	0.0155 (4)
O2	0.67770 (12)	0.38360 (18)	0.68702 (10)	0.0167 (4)
O3	0.75097 (11)	−0.09345 (18)	0.70015 (10)	0.0162 (4)
N1	0.76074 (14)	0.1326 (2)	0.74976 (12)	0.0155 (4)
H1	0.7445 (18)	0.2220 (14)	0.7429 (17)	0.021 (8)*
C1	0.83515 (16)	0.6177 (3)	0.71146 (15)	0.0135 (5)
C2	0.86804 (18)	0.6706 (3)	0.78784 (16)	0.0182 (6)
H2	0.8346	0.7352	0.8094	0.022*
C3	0.94956 (19)	0.6294 (3)	0.83297 (18)	0.0260 (6)
H3	0.9713	0.6659	0.8851	0.031*
C4	0.99895 (18)	0.5356 (3)	0.80199 (18)	0.0272 (7)
H4	1.0549	0.5090	0.8323	0.033*
C5	0.96632 (18)	0.4809 (3)	0.72680 (18)	0.0249 (6)
H5	0.9998	0.4160	0.7055	0.030*
C6	0.88493 (17)	0.5203 (3)	0.68220 (16)	0.0196 (6)
H6	0.8627	0.4803	0.6309	0.023*
C7	0.71739 (17)	0.7899 (3)	0.52981 (15)	0.0156 (5)
C8	0.79231 (19)	0.8554 (3)	0.52171 (17)	0.0212 (6)
H8	0.8436	0.8495	0.5636	0.025*
C9	0.7924 (2)	0.9291 (3)	0.45295 (18)	0.0283 (7)
H9	0.8441	0.9712	0.4479	0.034*
C10	0.7182 (2)	0.9418 (3)	0.39173 (17)	0.0286 (7)
H10	0.7187	0.9930	0.3450	0.034*
C11	0.6436 (2)	0.8797 (3)	0.39911 (17)	0.0275 (7)
H11	0.5922	0.8888	0.3575	0.033*
C12	0.64319 (19)	0.8035 (3)	0.46733 (17)	0.0221 (6)
H12	0.5915	0.7601	0.4714	0.026*
C13	0.59173 (17)	0.7011 (3)	0.65848 (15)	0.0149 (5)
C14	0.52338 (17)	0.6196 (3)	0.61153 (16)	0.0177 (5)
H14	0.5331	0.5557	0.5724	0.021*
C15	0.44184 (17)	0.6309 (3)	0.62125 (17)	0.0216 (6)
H15	0.3962	0.5747	0.5891	0.026*
C16	0.42711 (18)	0.7244 (3)	0.67808 (18)	0.0240 (6)
H16	0.3713	0.7320	0.6848	0.029*
C17	0.49320 (19)	0.8064 (3)	0.72480 (18)	0.0235 (6)
H17	0.4829	0.8708	0.7634	0.028*
C18	0.57512 (17)	0.7944 (3)	0.71517 (16)	0.0174 (5)
H18	0.6205	0.8507	0.7477	0.021*
C19	0.68113 (16)	0.3687 (3)	0.61824 (15)	0.0144 (5)
C20	0.67628 (18)	0.2192 (3)	0.57931 (16)	0.0183 (6)
H20A	0.7324	0.1979	0.5700	0.022*
H20B	0.6332	0.2238	0.5273	0.022*
C21	0.65302 (16)	0.0911 (3)	0.62635 (15)	0.0164 (5)
H21A	0.6050	0.1222	0.6470	0.020*
H21B	0.6324	0.0082	0.5898	0.020*
C22	0.72532 (16)	0.0370 (3)	0.69461 (15)	0.0141 (5)
C23	0.82697 (16)	0.0973 (3)	0.82208 (14)	0.0141 (5)
H23	0.8668	0.0238	0.8094	0.017*
C24	0.87745 (18)	0.2358 (3)	0.85281 (15)	0.0211 (6)
H24A	0.9053	0.2719	0.8132	0.025*
H24B	0.8377	0.3127	0.8608	0.025*
C25	0.94531 (18)	0.2078 (3)	0.93013 (16)	0.0205 (6)
H25A	0.9733	0.3016	0.9508	0.025*
H25B	0.9897	0.1416	0.9206	0.025*
C26	0.90676 (18)	0.1391 (3)	0.99144 (16)	0.0205 (6)
H26A	0.8679	0.2104	1.0062	0.025*
H26B	0.9532	0.1151	1.0394	0.025*
C27	0.85695 (18)	−0.0001 (3)	0.95937 (15)	0.0209 (6)
H27A	0.8968	−0.0749	0.9495	0.025*
H27B	0.8302	−0.0398	0.9990	0.025*
C28	0.78805 (16)	0.0314 (3)	0.88344 (15)	0.0181 (5)
H28A	0.7456	0.1005	0.8942	0.022*
H28B	0.7579	−0.0606	0.8628	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01279 (11)	0.00991 (10)	0.01152 (10)	0.00003 (6)	0.00211 (7)	0.00066 (6)
O1	0.0210 (10)	0.0116 (8)	0.0127 (9)	−0.0004 (7)	0.0027 (8)	0.0005 (7)
O2	0.0217 (10)	0.0125 (8)	0.0159 (10)	0.0022 (7)	0.0054 (8)	−0.0001 (7)
O3	0.0180 (10)	0.0100 (8)	0.0173 (9)	0.0000 (7)	−0.0006 (8)	−0.0013 (7)
N1	0.0185 (12)	0.0107 (10)	0.0141 (11)	0.0035 (8)	−0.0005 (9)	0.0009 (8)
C1	0.0144 (13)	0.0116 (11)	0.0142 (12)	0.0001 (9)	0.0033 (10)	0.0034 (9)
C2	0.0194 (14)	0.0130 (12)	0.0199 (14)	−0.0009 (10)	0.0016 (12)	−0.0001 (10)
C3	0.0270 (16)	0.0184 (13)	0.0247 (16)	−0.0065 (12)	−0.0059 (13)	0.0014 (12)
C4	0.0130 (14)	0.0244 (14)	0.0386 (18)	−0.0020 (11)	−0.0021 (13)	0.0127 (13)
C5	0.0193 (15)	0.0237 (14)	0.0355 (17)	0.0050 (11)	0.0141 (13)	0.0087 (12)
C6	0.0219 (14)	0.0209 (13)	0.0174 (14)	0.0021 (11)	0.0080 (12)	0.0041 (10)
C7	0.0222 (14)	0.0103 (11)	0.0133 (13)	−0.0007 (10)	0.0035 (11)	−0.0002 (9)
C8	0.0249 (15)	0.0187 (13)	0.0197 (14)	−0.0012 (11)	0.0055 (12)	0.0011 (11)
C9	0.0340 (17)	0.0231 (15)	0.0334 (18)	−0.0037 (12)	0.0184 (15)	0.0056 (12)
C10	0.0446 (19)	0.0237 (15)	0.0207 (15)	0.0027 (13)	0.0142 (14)	0.0055 (12)
C11	0.0346 (18)	0.0283 (15)	0.0155 (14)	0.0050 (13)	0.0000 (13)	0.0046 (12)
C12	0.0217 (15)	0.0250 (15)	0.0184 (14)	−0.0017 (11)	0.0037 (12)	0.0030 (11)
C13	0.0148 (13)	0.0130 (12)	0.0161 (13)	0.0002 (9)	0.0029 (11)	0.0039 (9)
C14	0.0168 (14)	0.0164 (12)	0.0181 (13)	−0.0002 (10)	0.0017 (11)	0.0005 (10)
C15	0.0145 (14)	0.0231 (14)	0.0238 (15)	−0.0023 (11)	−0.0005 (12)	0.0012 (11)
C16	0.0155 (14)	0.0279 (15)	0.0293 (16)	0.0024 (11)	0.0074 (13)	0.0027 (12)
C17	0.0250 (16)	0.0251 (15)	0.0228 (15)	0.0000 (11)	0.0105 (13)	−0.0028 (11)
C18	0.0161 (14)	0.0185 (13)	0.0167 (13)	−0.0026 (10)	0.0030 (11)	−0.0001 (10)
C19	0.0135 (13)	0.0123 (11)	0.0152 (13)	0.0004 (10)	0.0004 (10)	−0.0012 (10)
C20	0.0253 (15)	0.0131 (12)	0.0139 (13)	0.0005 (10)	0.0011 (11)	−0.0006 (10)
C21	0.0175 (13)	0.0107 (11)	0.0173 (13)	0.0002 (9)	−0.0014 (11)	−0.0003 (9)
C22	0.0130 (12)	0.0133 (11)	0.0163 (13)	−0.0010 (9)	0.0049 (10)	0.0015 (10)
C23	0.0145 (13)	0.0119 (11)	0.0134 (12)	0.0013 (9)	−0.0005 (10)	−0.0005 (9)
C24	0.0260 (15)	0.0170 (13)	0.0166 (14)	−0.0061 (11)	−0.0004 (12)	0.0000 (11)
C25	0.0220 (15)	0.0194 (13)	0.0163 (14)	−0.0064 (11)	−0.0006 (12)	0.0003 (10)
C26	0.0220 (15)	0.0230 (13)	0.0149 (13)	−0.0024 (11)	0.0024 (11)	−0.0006 (11)
C27	0.0229 (15)	0.0229 (13)	0.0163 (14)	−0.0042 (11)	0.0041 (12)	0.0044 (11)
C28	0.0154 (14)	0.0192 (13)	0.0190 (14)	−0.0008 (10)	0.0037 (11)	−0.0014 (10)

Geometric parameters (Å, º) top

Sn—O1	2.1658 (17)	C13—C14	1.401 (4)
Sn—O3ⁱ	2.3178 (16)	C14—C15	1.386 (4)
Sn—C1	2.138 (2)	C14—H14	0.9500
Sn—C7	2.129 (3)	C15—C16	1.388 (4)
Sn—C13	2.130 (3)	C15—H15	0.9500
O1—C19	1.291 (3)	C16—C17	1.379 (4)
O2—C19	1.239 (3)	C16—H16	0.9500
O3—C22	1.256 (3)	C17—C18	1.392 (4)
O3—Snⁱⁱ	2.3178 (16)	C17—H17	0.9500
N1—C22	1.316 (3)	C18—H18	0.9500
N1—C23	1.460 (3)	C19—C20	1.520 (3)
N1—H1	0.855 (10)	C20—C21	1.540 (3)
C1—C2	1.392 (4)	C20—H20A	0.9900
C1—C6	1.394 (3)	C20—H20B	0.9900
C2—C3	1.395 (4)	C21—C22	1.514 (3)
C2—H2	0.9500	C21—H21A	0.9900
C3—C4	1.386 (4)	C21—H21B	0.9900
C3—H3	0.9500	C23—C28	1.522 (3)
C4—C5	1.379 (4)	C23—C24	1.522 (3)
C4—H4	0.9500	C23—H23	1.0000
C5—C6	1.386 (4)	C24—C25	1.520 (4)
C5—H5	0.9500	C24—H24A	0.9900
C6—H6	0.9500	C24—H24B	0.9900
C7—C12	1.396 (4)	C25—C26	1.528 (4)
C7—C8	1.399 (4)	C25—H25A	0.9900
C8—C9	1.388 (4)	C25—H25B	0.9900
C8—H8	0.9500	C26—C27	1.528 (4)
C9—C10	1.384 (4)	C26—H26A	0.9900
C9—H9	0.9500	C26—H26B	0.9900
C10—C11	1.377 (4)	C27—C28	1.517 (4)
C10—H10	0.9500	C27—H27A	0.9900
C11—C12	1.392 (4)	C27—H27B	0.9900
C11—H11	0.9500	C28—H28A	0.9900
C12—H12	0.9500	C28—H28B	0.9900
C13—C18	1.396 (4)

C13—Sn—C7	112.66 (10)	C15—C16—H16	119.9
C13—Sn—C1	130.70 (10)	C16—C17—C18	119.8 (3)
C7—Sn—C1	115.46 (10)	C16—C17—H17	120.1
C13—Sn—O1	96.45 (8)	C18—C17—H17	120.1
C7—Sn—O1	89.56 (8)	C17—C18—C13	121.1 (3)
C1—Sn—O1	94.03 (8)	C17—C18—H18	119.4
C13—Sn—O3ⁱ	88.75 (8)	C13—C18—H18	119.4
C7—Sn—O3ⁱ	88.06 (8)	O2—C19—O1	123.4 (2)
C1—Sn—O3ⁱ	82.82 (8)	O2—C19—C20	122.1 (2)
O1—Sn—O3ⁱ	174.78 (6)	O1—C19—C20	114.6 (2)
C19—O1—Sn	113.42 (15)	C19—C20—C21	115.3 (2)
C22—O3—Snⁱⁱ	139.03 (17)	C19—C20—H20A	108.5
C22—N1—C23	124.5 (2)	C21—C20—H20A	108.5
C22—N1—H1	118 (2)	C19—C20—H20B	108.5
C23—N1—H1	117 (2)	C21—C20—H20B	108.5
C2—C1—C6	118.3 (2)	H20A—C20—H20B	107.5
C2—C1—Sn	122.91 (19)	C22—C21—C20	115.1 (2)
C6—C1—Sn	118.78 (19)	C22—C21—H21A	108.5
C1—C2—C3	120.6 (3)	C20—C21—H21A	108.5
C1—C2—H2	119.7	C22—C21—H21B	108.5
C3—C2—H2	119.7	C20—C21—H21B	108.5
C4—C3—C2	120.2 (3)	H21A—C21—H21B	107.5
C4—C3—H3	119.9	O3—C22—N1	120.2 (2)
C2—C3—H3	119.9	O3—C22—C21	122.6 (2)
C5—C4—C3	119.6 (3)	N1—C22—C21	117.2 (2)
C5—C4—H4	120.2	N1—C23—C28	111.0 (2)
C3—C4—H4	120.2	N1—C23—C24	108.8 (2)
C4—C5—C6	120.3 (3)	C28—C23—C24	111.3 (2)
C4—C5—H5	119.8	N1—C23—H23	108.6
C6—C5—H5	119.8	C28—C23—H23	108.6
C5—C6—C1	121.0 (3)	C24—C23—H23	108.6
C5—C6—H6	119.5	C25—C24—C23	111.5 (2)
C1—C6—H6	119.5	C25—C24—H24A	109.3
C12—C7—C8	117.8 (2)	C23—C24—H24A	109.3
C12—C7—Sn	120.59 (19)	C25—C24—H24B	109.3
C8—C7—Sn	121.5 (2)	C23—C24—H24B	109.3
C9—C8—C7	120.6 (3)	H24A—C24—H24B	108.0
C9—C8—H8	119.7	C24—C25—C26	111.6 (2)
C7—C8—H8	119.7	C24—C25—H25A	109.3
C10—C9—C8	120.8 (3)	C26—C25—H25A	109.3
C10—C9—H9	119.6	C24—C25—H25B	109.3
C8—C9—H9	119.6	C26—C25—H25B	109.3
C11—C10—C9	119.4 (3)	H25A—C25—H25B	108.0
C11—C10—H10	120.3	C25—C26—C27	110.9 (2)
C9—C10—H10	120.3	C25—C26—H26A	109.4
C10—C11—C12	120.2 (3)	C27—C26—H26A	109.4
C10—C11—H11	119.9	C25—C26—H26B	109.4
C12—C11—H11	119.9	C27—C26—H26B	109.4
C11—C12—C7	121.2 (3)	H26A—C26—H26B	108.0
C11—C12—H12	119.4	C28—C27—C26	110.8 (2)
C7—C12—H12	119.4	C28—C27—H27A	109.5
C18—C13—C14	118.0 (2)	C26—C27—H27A	109.5
C18—C13—Sn	123.41 (19)	C28—C27—H27B	109.5
C14—C13—Sn	118.57 (19)	C26—C27—H27B	109.5
C15—C14—C13	121.0 (3)	H27A—C27—H27B	108.1
C15—C14—H14	119.5	C27—C28—C23	110.7 (2)
C13—C14—H14	119.5	C27—C28—H28A	109.5
C14—C15—C16	119.8 (3)	C23—C28—H28A	109.5
C14—C15—H15	120.1	C27—C28—H28B	109.5
C16—C15—H15	120.1	C23—C28—H28B	109.5
C17—C16—C15	120.3 (3)	H28A—C28—H28B	108.1
C17—C16—H16	119.9

C13—Sn—O1—C19	−66.35 (18)	C1—Sn—C13—C18	61.5 (2)
C7—Sn—O1—C19	−179.11 (18)	O1—Sn—C13—C18	162.4 (2)
C1—Sn—O1—C19	65.40 (18)	O3ⁱ—Sn—C13—C18	−18.0 (2)
O3ⁱ—Sn—O1—C19	118.1 (7)	C7—Sn—C13—C14	71.7 (2)
C13—Sn—C1—C2	−47.4 (2)	C1—Sn—C13—C14	−121.5 (2)
C7—Sn—C1—C2	119.1 (2)	O1—Sn—C13—C14	−20.6 (2)
O1—Sn—C1—C2	−149.5 (2)	O3ⁱ—Sn—C13—C14	159.04 (19)
O3ⁱ—Sn—C1—C2	34.7 (2)	C18—C13—C14—C15	−0.2 (4)
C13—Sn—C1—C6	134.47 (19)	Sn—C13—C14—C15	−177.4 (2)
C7—Sn—C1—C6	−59.0 (2)	C13—C14—C15—C16	0.2 (4)
O1—Sn—C1—C6	32.4 (2)	C14—C15—C16—C17	0.1 (4)
O3ⁱ—Sn—C1—C6	−143.4 (2)	C15—C16—C17—C18	−0.4 (4)
C6—C1—C2—C3	1.5 (4)	C16—C17—C18—C13	0.4 (4)
Sn—C1—C2—C3	−176.64 (19)	C14—C13—C18—C17	−0.1 (4)
C1—C2—C3—C4	0.2 (4)	Sn—C13—C18—C17	176.9 (2)
C2—C3—C4—C5	−1.2 (4)	Sn—O1—C19—O2	6.9 (3)
C3—C4—C5—C6	0.5 (4)	Sn—O1—C19—C20	−172.26 (16)
C4—C5—C6—C1	1.3 (4)	O2—C19—C20—C21	9.0 (4)
C2—C1—C6—C5	−2.3 (4)	O1—C19—C20—C21	−171.8 (2)
Sn—C1—C6—C5	175.95 (19)	C19—C20—C21—C22	−77.3 (3)
C13—Sn—C7—C12	−28.0 (2)	Snⁱⁱ—O3—C22—N1	172.88 (17)
C1—Sn—C7—C12	163.02 (19)	Snⁱⁱ—O3—C22—C21	−6.3 (4)
O1—Sn—C7—C12	68.8 (2)	C23—N1—C22—O3	−3.6 (4)
O3ⁱ—Sn—C7—C12	−115.9 (2)	C23—N1—C22—C21	175.7 (2)
C13—Sn—C7—C8	148.0 (2)	C20—C21—C22—O3	−122.2 (3)
C1—Sn—C7—C8	−20.9 (2)	C20—C21—C22—N1	58.5 (3)
O1—Sn—C7—C8	−115.2 (2)	C22—N1—C23—C28	−81.0 (3)
O3ⁱ—Sn—C7—C8	60.2 (2)	C22—N1—C23—C24	156.2 (2)
C12—C7—C8—C9	−1.1 (4)	N1—C23—C24—C25	177.6 (2)
Sn—C7—C8—C9	−177.3 (2)	C28—C23—C24—C25	55.0 (3)
C7—C8—C9—C10	1.4 (4)	C23—C24—C25—C26	−54.0 (3)
C8—C9—C10—C11	−0.5 (4)	C24—C25—C26—C27	54.6 (3)
C9—C10—C11—C12	−0.6 (4)	C25—C26—C27—C28	−56.3 (3)
C10—C11—C12—C7	0.8 (4)	C26—C27—C28—C23	57.3 (3)
C8—C7—C12—C11	0.1 (4)	N1—C23—C28—C27	−178.0 (2)
Sn—C7—C12—C11	176.3 (2)	C24—C23—C28—C27	−56.7 (3)
C7—Sn—C13—C18	−105.3 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86 (1)	1.93 (2)	2.732 (3)	155 (3)

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₁₀H₁₆NO₃)]
M_r	548.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.2488 (12), 9.1243 (7), 17.6597 (13)
β (°)	106.101 (1)
V (Å³)	2515.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.634, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	23281, 5756, 4864
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.084, 1.03
No. of reflections	5756
No. of parameters	302
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.64

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn—O1	2.1658 (17)	Sn—C7	2.129 (3)
Sn—O3ⁱ	2.3178 (16)	Sn—C13	2.130 (3)
Sn—C1	2.138 (2)

Symmetry code: (i) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.855 (10)	1.932 (15)	2.732 (3)	155 (3)

Acknowledgements

We thank Allama Iqbal Open University and the University of Malaya for supporting this study.

References

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