catena-Poly[[triphenyl­tin(IV)]-μ-2-(cyclo­hexyl­amino­carbon­yl)benzoato-κ2O1:O2]

Imtiaz-ud-Din; Raqiqt-ul-Rasool; Bhatti, M.H.; Ng, S.W.

doi:10.1107/S1600536810026978

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m931

https://doi.org/10.1107/S1600536810026978

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catena-Poly[[triphenyltin(IV)]-μ-2-(cyclohexylaminocarbonyl)benzoato-κ²O¹:O²]

Imtiaz-ud-Din,^a Raqiqt-ul-Rasool,^a Moazzam H. Bhatti ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Allama Iqbal Open University, H/8 Islamabad, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 July 2010; accepted 7 July 2010; online 14 July 2010)

In the title polymeric complex, [Sn(C₆H₅)₃(C₁₄H₁₆NO₃)]_n, adjacent triphenyltin cations are bridged by the N-cyclohexylphthalamate anion through the carboxylate and carbonyl O atoms, forming a helical chain running along the b axis. The amide N atom is a hydrogen-bond donor to the uncoordinated carboxylate O atom. The geometry at the five-coordinate Sn atom is trans-C₃SnO₂ trigonal-bipyramidal.

Related literature

For a review on organotin carboxylates, see: Tiekink (1991 , 1994 ). Triphenyltin arylcarboxylates generally exist as monomeric molecules; see: Ng et al. (1986 ). For the synthesis of N-cyclohexylphthalamic acid, see: Dolzhenko et al. (2003 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₁₄H₁₆NO₃)]
M_r = 596.27
Monoclinic, P 2₁ /n
a = 9.8574 (5) Å
b = 16.0734 (8) Å
c = 17.1669 (8) Å
β = 99.447 (1)°
V = 2683.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 100 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.694, T_max = 0.827
25326 measured reflections
6165 independent reflections
5710 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.049
S = 1.02
6165 reflections
338 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.130 (1)
Sn1—C7	2.129 (2)
Sn1—C13	2.119 (1)
Sn1—O1	2.149 (1)
Sn1—O3ⁱ	2.392 (1)

O1—Sn1—O3ⁱ	174.06 (4)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86 (1)	1.85 (1)	2.666 (2)	158 (2)

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/S1600536810026978/xu2796sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026978/xu2796Isup2.hkl

checkCIF report

Comment top

Triphenyltin aryl-carboxylates commonly exist as four-coordinate tetrahedral compounds unlike the alkyl-carboxylates, which adopt carboxylate-bridged polymeric chains structures (Ng et al., 1986). Occasionally, the aryl-carboxylate anion bears a potential donor unit such as, in the present case, an amido group; such a donor group can interact with adjacent molecules to generate polymeric chain motifs (Tiekink, 1991; 1994). In the present N-cyclohexylphthalimic acid derivative (Scheme I), the amido oxygen atom engages in bonding to generate a chain motif (Fig. 1). The tin atom is displaced out of the C₃Sn girdle in the direction of the covalently-bonded oxygen atom by 0.200 (1) Å; the Sn–O_covalent bond is significantly shorter than the Sn–O_dative bond.

Related literature top

For a review on organotin carboxylates, see: Tiekink (1991, 1994). Triphenyltin arylcarboxylates generally exist as monomeric molecules; see: Ng et al. (1986). For the synthesis of N-cyclohexylphthalamic acid, see: Dolzhenko et al. (2003).

Experimental top

N-Cyclohexylphthalamic acid was synthesized from the reaction of phthalic anhydride and cyclohexylamine in ethyl acetate by using a reported procedure (Dolzhenko et al., 2003).

Triphenyltin hydroxide (1 mmol, 0.37 g) and N-cyclohexylphthalamic acid (1 mmol, 0.25 g) were heated in toluene (50 ml) for 6 h in a Dean-Stark water-separator. The solvent was then removed and the solid material recrystallized from a chloroform and n-hexane (3:1) mixture to furnish crystals.

Structure description top

For a review on organotin carboxylates, see: Tiekink (1991, 1994). Triphenyltin arylcarboxylates generally exist as monomeric molecules; see: Ng et al. (1986). For the synthesis of N-cyclohexylphthalamic acid, see: Dolzhenko et al. (2003).

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 a portion of polymeric Sn(C₆H₅)₃(C₁₄H₁₆NO₃) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

catena-Poly[[triphenyltin(IV)]-µ-2- (cyclohexylaminocarbonyl)benzoato-κ²O¹:O²] top

Crystal data top

[Sn(C₆H₅)₃(C₁₄H₁₆NO₃)]	F(000) = 1216
M_r = 596.27	D_x = 1.476 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9925 reflections
a = 9.8574 (5) Å	θ = 2.4–28.3°
b = 16.0734 (8) Å	µ = 0.99 mm⁻¹
c = 17.1669 (8) Å	T = 100 K
β = 99.447 (1)°	Block, colorless
V = 2683.1 (2) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	6165 independent reflections
Radiation source: fine-focus sealed tube	5710 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.694, T_max = 0.827	k = −20→20
25326 measured reflections	l = −22→21

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0227P)² + 1.7091P] where P = (F_o² + 2F_c²)/3
6165 reflections	(Δ/σ)_max = 0.001
338 parameters	Δρ_max = 0.35 e Å⁻³
1 restraint	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₁₄H₁₆NO₃)]	V = 2683.1 (2) Å³
M_r = 596.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8574 (5) Å	µ = 0.99 mm⁻¹
b = 16.0734 (8) Å	T = 100 K
c = 17.1669 (8) Å	0.40 × 0.30 × 0.20 mm
β = 99.447 (1)°

Data collection top

Bruker SMART APEX diffractometer	6165 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5710 reflections with I > 2σ(I)
T_min = 0.694, T_max = 0.827	R_int = 0.023
25326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	1 restraint
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.35 e Å⁻³
6165 reflections	Δρ_min = −0.50 e Å⁻³
338 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.914994 (9)	0.372319 (5)	0.750433 (5)	0.01199 (4)
O1	0.88805 (10)	0.26134 (6)	0.67977 (6)	0.0167 (2)
O2	0.66233 (11)	0.26088 (6)	0.67972 (6)	0.0181 (2)
O3	0.53077 (10)	−0.00855 (6)	0.66684 (6)	0.0160 (2)
N1	0.51088 (14)	0.12682 (7)	0.69698 (8)	0.0177 (3)
H1	0.5391 (19)	0.1765 (7)	0.6891 (11)	0.022 (5)*
C1	0.78221 (14)	0.45043 (8)	0.67164 (8)	0.0150 (3)
C2	0.78027 (18)	0.44190 (10)	0.59071 (9)	0.0242 (3)
H2	0.8315	0.3985	0.5717	0.029*
C3	0.70416 (19)	0.49620 (11)	0.53752 (10)	0.0293 (4)
H3	0.7034	0.4895	0.4825	0.035*
C4	0.62957 (17)	0.55996 (10)	0.56442 (10)	0.0257 (3)
H4	0.5788	0.5975	0.5280	0.031*
C5	0.62943 (15)	0.56869 (9)	0.64469 (10)	0.0209 (3)
H5	0.5781	0.6122	0.6635	0.025*
C6	0.70430 (14)	0.51388 (9)	0.69779 (9)	0.0170 (3)
H6	0.7024	0.5197	0.7527	0.020*
C7	1.12405 (15)	0.37813 (8)	0.73368 (9)	0.0143 (3)
C8	1.22988 (15)	0.39979 (9)	0.79465 (9)	0.0175 (3)
H8	1.2096	0.4093	0.8461	0.021*
C9	1.36463 (16)	0.40761 (10)	0.78118 (10)	0.0230 (3)
H9	1.4356	0.4216	0.8236	0.028*
C10	1.39583 (16)	0.39509 (9)	0.70631 (10)	0.0232 (3)
H10	1.4880	0.4002	0.6973	0.028*
C11	1.29187 (18)	0.37515 (9)	0.64477 (10)	0.0230 (3)
H11	1.3124	0.3677	0.5931	0.028*
C12	1.15697 (16)	0.36592 (9)	0.65838 (9)	0.0188 (3)
H12	1.0866	0.3512	0.6159	0.023*
C13	0.85936 (15)	0.32474 (8)	0.85593 (8)	0.0147 (3)
C14	0.72102 (16)	0.32227 (9)	0.86407 (9)	0.0180 (3)
H14	0.6523	0.3338	0.8198	0.022*
C15	0.68262 (17)	0.30300 (10)	0.93644 (9)	0.0226 (3)
H15	0.5880	0.3018	0.9413	0.027*
C16	0.78136 (19)	0.28563 (10)	1.00104 (9)	0.0245 (3)
H16	0.7549	0.2737	1.0506	0.029*
C17	0.91974 (18)	0.28560 (10)	0.99353 (9)	0.0244 (3)
H17	0.9878	0.2718	1.0375	0.029*
C18	0.95815 (16)	0.30584 (9)	0.92144 (9)	0.0198 (3)
H18	1.0528	0.3068	0.9168	0.024*
C19	0.76680 (15)	0.22960 (8)	0.66099 (8)	0.0144 (3)
C20	0.76215 (15)	0.15244 (9)	0.60958 (8)	0.0140 (3)
C21	0.86142 (16)	0.15062 (10)	0.55998 (9)	0.0195 (3)
H21	0.9268	0.1944	0.5633	0.023*
C22	0.86751 (17)	0.08691 (10)	0.50612 (9)	0.0224 (3)
H22	0.9354	0.0877	0.4727	0.027*
C23	0.77383 (17)	0.02216 (9)	0.50143 (9)	0.0200 (3)
H23	0.7757	−0.0212	0.4640	0.024*
C24	0.67742 (15)	0.02117 (9)	0.55164 (8)	0.0161 (3)
H24	0.6152	−0.0243	0.5490	0.019*
C25	0.66847 (14)	0.08489 (8)	0.60619 (8)	0.0132 (3)
C26	0.56431 (14)	0.06626 (8)	0.66012 (8)	0.0134 (3)
C27	0.41889 (15)	0.11215 (9)	0.75476 (9)	0.0181 (3)
H27	0.4034	0.0509	0.7585	0.022*
C28	0.48651 (19)	0.14361 (12)	0.83514 (10)	0.0293 (4)
H28A	0.5067	0.2037	0.8317	0.035*
H28B	0.5746	0.1140	0.8516	0.035*
C29	0.3924 (2)	0.12963 (12)	0.89671 (11)	0.0342 (4)
H29A	0.3791	0.0692	0.9036	0.041*
H29B	0.4365	0.1528	0.9481	0.041*
C30	0.2540 (2)	0.17094 (11)	0.87143 (12)	0.0337 (4)
H30A	0.1931	0.1578	0.9103	0.040*
H30B	0.2664	0.2320	0.8708	0.040*
C31	0.18684 (19)	0.14199 (13)	0.79050 (13)	0.0357 (4)
H31A	0.1005	0.1734	0.7742	0.043*
H31B	0.1630	0.0823	0.7930	0.043*
C32	0.28089 (18)	0.15421 (12)	0.72883 (11)	0.0298 (4)
H32B	0.2364	0.1305	0.6777	0.036*
H32C	0.2952	0.2144	0.7212	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01138 (5)	0.01205 (5)	0.01288 (5)	0.00013 (3)	0.00303 (4)	0.00005 (3)
O1	0.0158 (5)	0.0156 (5)	0.0186 (5)	−0.0014 (4)	0.0025 (4)	−0.0032 (4)
O2	0.0180 (5)	0.0149 (5)	0.0229 (5)	−0.0007 (4)	0.0081 (4)	−0.0011 (4)
O3	0.0181 (5)	0.0133 (4)	0.0169 (5)	−0.0009 (4)	0.0042 (4)	0.0016 (4)
N1	0.0202 (6)	0.0132 (6)	0.0222 (6)	−0.0013 (5)	0.0109 (5)	0.0013 (5)
C1	0.0143 (7)	0.0140 (6)	0.0167 (7)	−0.0009 (5)	0.0019 (5)	0.0015 (5)
C2	0.0300 (9)	0.0236 (8)	0.0195 (8)	0.0096 (6)	0.0057 (6)	0.0005 (6)
C3	0.0373 (10)	0.0334 (9)	0.0171 (7)	0.0116 (7)	0.0040 (7)	0.0050 (7)
C4	0.0249 (8)	0.0257 (8)	0.0262 (8)	0.0068 (6)	0.0035 (6)	0.0092 (6)
C5	0.0152 (7)	0.0186 (7)	0.0296 (8)	0.0033 (5)	0.0056 (6)	0.0011 (6)
C6	0.0129 (6)	0.0201 (7)	0.0185 (7)	−0.0011 (5)	0.0038 (5)	−0.0020 (5)
C7	0.0144 (6)	0.0116 (6)	0.0175 (7)	0.0009 (5)	0.0042 (5)	0.0000 (5)
C8	0.0175 (7)	0.0176 (7)	0.0178 (7)	0.0014 (5)	0.0043 (6)	−0.0015 (5)
C9	0.0158 (7)	0.0223 (7)	0.0300 (8)	0.0001 (6)	0.0012 (6)	−0.0013 (6)
C10	0.0166 (7)	0.0176 (7)	0.0379 (9)	−0.0013 (6)	0.0124 (7)	0.0003 (6)
C11	0.0278 (8)	0.0197 (7)	0.0253 (8)	−0.0019 (6)	0.0158 (7)	−0.0014 (6)
C12	0.0203 (7)	0.0189 (7)	0.0180 (7)	−0.0022 (5)	0.0056 (6)	−0.0029 (5)
C13	0.0188 (7)	0.0112 (6)	0.0147 (6)	0.0001 (5)	0.0045 (5)	−0.0009 (5)
C14	0.0189 (7)	0.0193 (7)	0.0162 (7)	0.0014 (5)	0.0041 (5)	0.0000 (5)
C15	0.0255 (8)	0.0217 (7)	0.0235 (8)	−0.0008 (6)	0.0126 (6)	−0.0014 (6)
C16	0.0410 (10)	0.0182 (7)	0.0157 (7)	−0.0039 (6)	0.0089 (7)	0.0003 (6)
C17	0.0353 (9)	0.0184 (7)	0.0168 (7)	−0.0028 (6)	−0.0040 (6)	0.0025 (6)
C18	0.0200 (7)	0.0161 (7)	0.0222 (7)	−0.0018 (5)	0.0005 (6)	0.0007 (6)
C19	0.0185 (7)	0.0131 (6)	0.0122 (6)	−0.0005 (5)	0.0039 (5)	0.0022 (5)
C20	0.0155 (7)	0.0136 (6)	0.0130 (6)	0.0003 (5)	0.0023 (5)	0.0006 (5)
C21	0.0217 (8)	0.0189 (7)	0.0195 (7)	−0.0046 (6)	0.0078 (6)	−0.0020 (6)
C22	0.0274 (8)	0.0230 (7)	0.0200 (7)	−0.0026 (6)	0.0133 (6)	−0.0022 (6)
C23	0.0290 (8)	0.0168 (7)	0.0156 (7)	−0.0002 (6)	0.0074 (6)	−0.0027 (5)
C24	0.0194 (7)	0.0143 (6)	0.0142 (6)	−0.0014 (5)	0.0018 (5)	0.0006 (5)
C25	0.0132 (6)	0.0142 (6)	0.0120 (6)	0.0010 (5)	0.0019 (5)	0.0017 (5)
C26	0.0125 (6)	0.0151 (6)	0.0121 (6)	0.0002 (5)	0.0005 (5)	0.0020 (5)
C27	0.0206 (7)	0.0134 (6)	0.0234 (8)	0.0004 (5)	0.0126 (6)	0.0019 (5)
C28	0.0249 (9)	0.0423 (10)	0.0231 (8)	−0.0018 (7)	0.0113 (7)	−0.0007 (7)
C29	0.0366 (10)	0.0444 (11)	0.0260 (9)	−0.0012 (8)	0.0181 (8)	0.0011 (7)
C30	0.0437 (11)	0.0218 (8)	0.0447 (11)	0.0067 (7)	0.0340 (9)	0.0064 (7)
C31	0.0211 (9)	0.0427 (10)	0.0480 (12)	0.0074 (7)	0.0194 (8)	0.0164 (9)
C32	0.0207 (8)	0.0401 (9)	0.0310 (9)	0.0039 (7)	0.0118 (7)	0.0107 (8)

Geometric parameters (Å, º) top

Sn1—C1	2.130 (1)	C14—H14	0.9500
Sn1—C7	2.129 (2)	C15—C16	1.379 (2)
Sn1—C13	2.119 (1)	C15—H15	0.9500
Sn1—O1	2.149 (1)	C16—C17	1.391 (3)
Sn1—O3ⁱ	2.392 (1)	C16—H16	0.9500
O1—C19	1.2908 (17)	C17—C18	1.391 (2)
O2—C19	1.2350 (18)	C17—H17	0.9500
O3—C26	1.2574 (17)	C18—H18	0.9500
O3—Sn1ⁱⁱ	2.3917 (10)	C19—C20	1.5186 (19)
N1—C26	1.3171 (18)	C20—C21	1.399 (2)
N1—C27	1.4687 (18)	C20—C25	1.4204 (19)
N1—H1	0.864 (9)	C21—C22	1.388 (2)
C1—C6	1.395 (2)	C21—H21	0.9500
C1—C2	1.393 (2)	C22—C23	1.385 (2)
C2—C3	1.391 (2)	C22—H22	0.9500
C2—H2	0.9500	C23—C24	1.384 (2)
C3—C4	1.384 (2)	C23—H23	0.9500
C3—H3	0.9500	C24—C25	1.4004 (19)
C4—C5	1.385 (2)	C24—H24	0.9500
C4—H4	0.9500	C25—C26	1.5208 (19)
C5—C6	1.390 (2)	C27—C32	1.519 (2)
C5—H5	0.9500	C27—C28	1.517 (2)
C6—H6	0.9500	C27—H27	1.0000
C7—C8	1.395 (2)	C28—C29	1.533 (2)
C7—C12	1.397 (2)	C28—H28A	0.9900
C8—C9	1.391 (2)	C28—H28B	0.9900
C8—H8	0.9500	C29—C30	1.515 (3)
C9—C10	1.385 (2)	C29—H29A	0.9900
C9—H9	0.9500	C29—H29B	0.9900
C10—C11	1.383 (2)	C30—C31	1.511 (3)
C10—H10	0.9500	C30—H30A	0.9900
C11—C12	1.395 (2)	C30—H30B	0.9900
C11—H11	0.9500	C31—C32	1.530 (2)
C12—H12	0.9500	C31—H31A	0.9900
C13—C14	1.394 (2)	C31—H31B	0.9900
C13—C18	1.395 (2)	C32—H32B	0.9900
C14—C15	1.392 (2)	C32—H32C	0.9900

C13—Sn1—C7	121.55 (6)	C16—C17—H17	120.1
C13—Sn1—C1	122.49 (5)	C17—C18—C13	120.82 (15)
C7—Sn1—C1	113.32 (5)	C17—C18—H18	119.6
C13—Sn1—O1	99.06 (5)	C13—C18—H18	119.6
C7—Sn1—O1	89.59 (5)	O2—C19—O1	123.47 (13)
C1—Sn1—O1	97.16 (5)	O2—C19—C20	122.47 (13)
C13—Sn1—O3ⁱ	81.11 (4)	O1—C19—C20	113.98 (12)
C7—Sn1—O3ⁱ	85.30 (4)	C21—C20—C25	118.31 (13)
C1—Sn1—O3ⁱ	87.67 (4)	C21—C20—C19	114.42 (12)
O1—Sn1—O3ⁱ	174.06 (4)	C25—C20—C19	127.27 (12)
C19—O1—Sn1	119.52 (9)	C22—C21—C20	122.14 (14)
C26—O3—Sn1ⁱⁱ	141.59 (9)	C22—C21—H21	118.9
C26—N1—C27	123.08 (12)	C20—C21—H21	118.9
C26—N1—H1	116.4 (13)	C21—C22—C23	119.47 (14)
C27—N1—H1	120.3 (13)	C21—C22—H22	120.3
C6—C1—C2	118.35 (13)	C23—C22—H22	120.3
C6—C1—Sn1	122.69 (11)	C24—C23—C22	119.46 (13)
C2—C1—Sn1	118.80 (11)	C24—C23—H23	120.3
C3—C2—C1	120.72 (14)	C22—C23—H23	120.3
C3—C2—H2	119.6	C23—C24—C25	122.23 (13)
C1—C2—H2	119.6	C23—C24—H24	118.9
C4—C3—C2	120.30 (15)	C25—C24—H24	118.9
C4—C3—H3	119.8	C24—C25—C20	118.33 (13)
C2—C3—H3	119.8	C24—C25—C26	112.71 (12)
C3—C4—C5	119.62 (15)	C20—C25—C26	128.68 (12)
C3—C4—H4	120.2	O3—C26—N1	122.06 (13)
C5—C4—H4	120.2	O3—C26—C25	117.27 (12)
C4—C5—C6	120.08 (14)	N1—C26—C25	120.67 (12)
C4—C5—H5	120.0	N1—C27—C32	110.68 (12)
C6—C5—H5	120.0	N1—C27—C28	109.45 (13)
C1—C6—C5	120.91 (14)	C32—C27—C28	110.90 (14)
C1—C6—H6	119.5	N1—C27—H27	108.6
C5—C6—H6	119.5	C32—C27—H27	108.6
C8—C7—C12	118.07 (14)	C28—C27—H27	108.6
C8—C7—Sn1	122.05 (11)	C27—C28—C29	110.67 (15)
C12—C7—Sn1	119.72 (11)	C27—C28—H28A	109.5
C9—C8—C7	120.98 (14)	C29—C28—H28A	109.5
C9—C8—H8	119.5	C27—C28—H28B	109.5
C7—C8—H8	119.5	C29—C28—H28B	109.5
C10—C9—C8	120.32 (15)	H28A—C28—H28B	108.1
C10—C9—H9	119.8	C30—C29—C28	110.89 (15)
C8—C9—H9	119.8	C30—C29—H29A	109.5
C9—C10—C11	119.54 (14)	C28—C29—H29A	109.5
C9—C10—H10	120.2	C30—C29—H29B	109.5
C11—C10—H10	120.2	C28—C29—H29B	109.5
C10—C11—C12	120.25 (15)	H29A—C29—H29B	108.0
C10—C11—H11	119.9	C31—C30—C29	111.49 (15)
C12—C11—H11	119.9	C31—C30—H30A	109.3
C11—C12—C7	120.82 (15)	C29—C30—H30A	109.3
C11—C12—H12	119.6	C31—C30—H30B	109.3
C7—C12—H12	119.6	C29—C30—H30B	109.3
C14—C13—C18	118.56 (13)	H30A—C30—H30B	108.0
C14—C13—Sn1	119.37 (10)	C30—C31—C32	111.89 (16)
C18—C13—Sn1	121.55 (11)	C30—C31—H31A	109.2
C15—C14—C13	120.64 (14)	C32—C31—H31A	109.2
C15—C14—H14	119.7	C30—C31—H31B	109.2
C13—C14—H14	119.7	C32—C31—H31B	109.2
C16—C15—C14	120.24 (15)	H31A—C31—H31B	107.9
C16—C15—H15	119.9	C27—C32—C31	110.81 (14)
C14—C15—H15	119.9	C27—C32—H32B	109.5
C15—C16—C17	119.93 (14)	C31—C32—H32B	109.5
C15—C16—H16	120.0	C27—C32—H32C	109.5
C17—C16—H16	120.0	C31—C32—H32C	109.5
C18—C17—C16	119.78 (15)	H32B—C32—H32C	108.1
C18—C17—H17	120.1

C13—Sn1—O1—C19	64.82 (11)	C18—C13—C14—C15	1.3 (2)
C7—Sn1—O1—C19	−173.26 (10)	Sn1—C13—C14—C15	−170.53 (11)
C1—Sn1—O1—C19	−59.80 (10)	C13—C14—C15—C16	−0.4 (2)
C13—Sn1—C1—C6	41.13 (14)	C14—C15—C16—C17	−1.4 (2)
C7—Sn1—C1—C6	−120.66 (12)	C15—C16—C17—C18	2.1 (2)
O1—Sn1—C1—C6	146.69 (11)	C16—C17—C18—C13	−1.2 (2)
O3ⁱ—Sn1—C1—C6	−36.79 (12)	C14—C13—C18—C17	−0.5 (2)
C13—Sn1—C1—C2	−143.59 (12)	Sn1—C13—C18—C17	171.13 (11)
C7—Sn1—C1—C2	54.62 (13)	Sn1—O1—C19—O2	2.02 (18)
O1—Sn1—C1—C2	−38.03 (13)	Sn1—O1—C19—C20	178.78 (8)
O3ⁱ—Sn1—C1—C2	138.49 (12)	O2—C19—C20—C21	146.62 (14)
C6—C1—C2—C3	1.0 (2)	O1—C19—C20—C21	−30.18 (18)
Sn1—C1—C2—C3	−174.49 (14)	O2—C19—C20—C25	−32.3 (2)
C1—C2—C3—C4	0.3 (3)	O1—C19—C20—C25	150.90 (14)
C2—C3—C4—C5	−1.0 (3)	C25—C20—C21—C22	2.4 (2)
C3—C4—C5—C6	0.3 (3)	C19—C20—C21—C22	−176.59 (14)
C2—C1—C6—C5	−1.7 (2)	C20—C21—C22—C23	−0.8 (2)
Sn1—C1—C6—C5	173.61 (11)	C21—C22—C23—C24	−1.3 (2)
C4—C5—C6—C1	1.1 (2)	C22—C23—C24—C25	1.7 (2)
C13—Sn1—C7—C8	−38.88 (13)	C23—C24—C25—C20	−0.1 (2)
C1—Sn1—C7—C8	123.10 (11)	C23—C24—C25—C26	−174.48 (13)
O1—Sn1—C7—C8	−139.28 (11)	C21—C20—C25—C24	−2.0 (2)
O3ⁱ—Sn1—C7—C8	37.67 (11)	C19—C20—C25—C24	176.91 (13)
C13—Sn1—C7—C12	145.85 (10)	C21—C20—C25—C26	171.43 (14)
C1—Sn1—C7—C12	−52.17 (12)	C19—C20—C25—C26	−9.7 (2)
O1—Sn1—C7—C12	45.45 (11)	Sn1ⁱⁱ—O3—C26—N1	−85.49 (19)
O3ⁱ—Sn1—C7—C12	−137.60 (11)	Sn1ⁱⁱ—O3—C26—C25	95.48 (16)
C12—C7—C8—C9	−1.1 (2)	C27—N1—C26—O3	6.3 (2)
Sn1—C7—C8—C9	−176.43 (11)	C27—N1—C26—C25	−174.74 (13)
C7—C8—C9—C10	0.9 (2)	C24—C25—C26—O3	20.40 (18)
C8—C9—C10—C11	0.3 (2)	C20—C25—C26—O3	−153.31 (14)
C9—C10—C11—C12	−1.4 (2)	C24—C25—C26—N1	−158.65 (13)
C10—C11—C12—C7	1.2 (2)	C20—C25—C26—N1	27.6 (2)
C8—C7—C12—C11	0.0 (2)	C26—N1—C27—C32	−121.11 (16)
Sn1—C7—C12—C11	175.48 (11)	C26—N1—C27—C28	116.37 (16)
C7—Sn1—C13—C14	179.98 (10)	N1—C27—C28—C29	179.65 (14)
C1—Sn1—C13—C14	19.66 (13)	C32—C27—C28—C29	57.26 (19)
O1—Sn1—C13—C14	−84.89 (11)	C27—C28—C29—C30	−56.6 (2)
O3ⁱ—Sn1—C13—C14	101.13 (11)	C28—C29—C30—C31	55.2 (2)
C7—Sn1—C13—C18	8.41 (14)	C29—C30—C31—C32	−54.5 (2)
C1—Sn1—C13—C18	−151.91 (11)	N1—C27—C32—C31	−177.73 (15)
O1—Sn1—C13—C18	103.54 (11)	C28—C27—C32—C31	−56.1 (2)
O3ⁱ—Sn1—C13—C18	−70.44 (11)	C30—C31—C32—C27	54.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86 (1)	1.85 (1)	2.666 (2)	158 (2)

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₁₄H₁₆NO₃)]
M_r	596.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.8574 (5), 16.0734 (8), 17.1669 (8)
β (°)	99.447 (1)
V (Å³)	2683.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.694, 0.827
No. of measured, independent and observed [I > 2σ(I)] reflections	25326, 6165, 5710
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.049, 1.02
No. of reflections	6165
No. of parameters	338
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)	0.35, −0.50

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

Selected geometric parameters (Å, º) top

Sn1—C1	2.130 (1)	Sn1—O1	2.149 (1)
Sn1—C7	2.129 (2)	Sn1—O3ⁱ	2.392 (1)
Sn1—C13	2.119 (1)

O1—Sn1—O3ⁱ	174.06 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86 (1)	1.85 (1)	2.666 (2)	158 (2)

Acknowledgements

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

References

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