catena-Poly[[tris­(4-fluoro­benz­yl)tin(IV)]-μ-2-[(piperidin-1-yl)carbothio­ylsulfan­yl]acetato-κ2O:O′]

Keng, C.T.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810028321

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m978

https://doi.org/10.1107/S1600536810028321

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catena-Poly[[tris(4-fluorobenzyl)tin(IV)]-μ-2-[(piperidin-1-yl)carbothioylsulfanyl]acetato-κ²O:O′]

Chun Thy Keng,^a 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 14 July 2010; accepted 15 July 2010; online 21 July 2010)

Adjacent units of the title polymeric complex, [Sn(C₇H₆F)₃(C₈H₁₂NO₂S₂)], are bridged by the carboxylate ion into a helical chain running along the b axis. The Sn(IV) atom shows a distorted trans-C₃SnO₂ trigonal-bipyramidal coordination and is displaced by 0.113 (2) Å out of the C₃Sn girdle in the direction of the covalently bonded O atom. The ring is disordered of two positions with an occupancy of 0.631 (4) for the major occupied site.

Related literature

For a comment on the repeat distance of carboxylate-bridged trialkyltin carboxylates, see: Ng et al. (1989 ).

Experimental

Crystal data

[Sn(C₇H₆F)₃(C₈H₁₂NO₂S₂)]
M_r = 664.35
Monoclinic, P 2₁ /n
a = 11.8016 (7) Å
b = 10.4572 (6) Å
c = 23.0334 (13) Å
β = 94.013 (1)°
V = 2835.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.10 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.735, T_max = 0.811
25437 measured reflections
6498 independent reflections
5328 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.077
S = 1.05
6498 reflections
371 parameters
17 restraints
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −1.19 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.144 (3)
Sn1—C8	2.155 (3)
Sn1—C15	2.158 (3)
Sn1—O1	2.175 (2)
Sn1—O2ⁱ	2.339 (2)

O1—Sn1—O2ⁱ	170.59 (7)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536810028321/bt5300sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028321/bt5300Isup2.hkl

checkCIF report

Comment top

Trialkyltin carboxylates generally adopt linear carboxylate-bridged motifs; the repeat distance of such polymers is independent of the nature of the carboxylate group. This feature of trialkyltin carboxylates is also borne out in tris(4-fluorobenzyl)tin (N-pentamethylenecarbamothio)sulfanylacetate (Scheme I), whose repeat distance, i.e., half the b-axis, of 5.23 Å, falls within the range of repeat distances reported (Ng et al., 1989). The tin atom shows trans-C₃SnO₂ trigonal bipyramidal coordination; the tin atom is displaced by 0.113 (2) Å out of the C₃Sn girdle in the direction of the covalently-bonded oxygen atom. The O-Sn-O angle is close to linearity (Table 1).

Related literature top

For a comment on the repeat distance of carboxylate-bridged trialkyltin carboxylates, see: Ng et al. (1989).

Experimental top

Tris(4-fluorobenzyl)tin hydroxide was prepared by hydrolysis of tris(4-fluorobenzyl)tin chloride in dilute sodium hydroxide. The hydroxide (1.0 g, 2.2 mmol) and N-piperinyldithiocarbamylacetic acid (0.48 g, 2.2 mmol) were heated in ethanol for an hour. The solution was filtered and then set aside for the growth of crystals.

Structure description top

For a comment on the repeat distance of carboxylate-bridged trialkyltin carboxylates, see: Ng et al. (1989).

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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of a portion of polymeric [Sn(C₇H₆F)₃(C₈H₁₂NO₂S₂)]_n; ellipsoids are drawn at the 70% probability level and H atoms are of arbitrary radius. The disorder is not shown. Symmetry code is given in Table 1.

catena-Poly[[tris(4-fluorobenzyl)tin(IV)]-µ-2-[(piperidin-1- yl)carbothioylsulfanyl]acetato-κ²O:O'] top

Crystal data top

[Sn(C₇H₆F)₃(C₈H₁₂NO₂S₂)]	F(000) = 1344
M_r = 664.35	D_x = 1.556 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9852 reflections
a = 11.8016 (7) Å	θ = 2.4–28.3°
b = 10.4572 (6) Å	µ = 1.10 mm⁻¹
c = 23.0334 (13) Å	T = 100 K
β = 94.013 (1)°	Prism, colorless
V = 2835.6 (3) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	6498 independent reflections
Radiation source: fine-focus sealed tube	5328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.735, T_max = 0.811	k = −13→13
25437 measured reflections	l = −29→29

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0254P)² + 5.3214P] where P = (F_o² + 2F_c²)/3
6498 reflections	(Δ/σ)_max = 0.001
371 parameters	Δρ_max = 0.50 e Å⁻³
17 restraints	Δρ_min = −1.19 e Å⁻³

Crystal data top

[Sn(C₇H₆F)₃(C₈H₁₂NO₂S₂)]	V = 2835.6 (3) Å³
M_r = 664.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8016 (7) Å	µ = 1.10 mm⁻¹
b = 10.4572 (6) Å	T = 100 K
c = 23.0334 (13) Å	0.30 × 0.25 × 0.20 mm
β = 94.013 (1)°

Data collection top

Bruker SMART APEX diffractometer	6498 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5328 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.811	R_int = 0.038
25437 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	17 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.05	Δρ_max = 0.50 e Å⁻³
6498 reflections	Δρ_min = −1.19 e Å⁻³
371 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.710443 (15)	0.543605 (18)	0.737119 (9)	0.01476 (6)
S1	0.57734 (6)	0.05444 (7)	0.62134 (3)	0.01883 (15)
S2	0.68919 (7)	0.25659 (8)	0.55248 (4)	0.02778 (18)
F1	0.20300 (17)	0.7560 (2)	0.79264 (11)	0.0494 (6)
F2	0.2292 (2)	0.5457 (3)	0.56053 (13)	0.0778 (10)
F3	1.0169 (2)	0.7386 (2)	0.52170 (10)	0.0508 (6)
O1	0.61265 (18)	0.39691 (19)	0.68910 (10)	0.0219 (5)
O2	0.71042 (17)	0.22277 (19)	0.71464 (9)	0.0199 (4)
N1	0.7199 (2)	0.0057 (3)	0.54087 (13)	0.0219 (9)	0.631 (4)
N1'	0.6619 (3)	0.0131 (4)	0.52047 (19)	0.0219 (9)	0.37
C1	0.6237 (2)	0.5024 (3)	0.81369 (13)	0.0203 (6)
H1A	0.6141	0.4088	0.8174	0.024*
H1B	0.6699	0.5330	0.8485	0.024*
C2	0.5100 (2)	0.5657 (3)	0.81084 (13)	0.0194 (6)
C3	0.4159 (3)	0.5111 (3)	0.78054 (14)	0.0244 (7)
H3	0.4231	0.4294	0.7632	0.029*
C4	0.3121 (3)	0.5734 (4)	0.77516 (16)	0.0318 (8)
H4	0.2479	0.5347	0.7551	0.038*
C5	0.3044 (3)	0.6923 (4)	0.79952 (16)	0.0316 (8)
C6	0.3936 (3)	0.7503 (3)	0.83053 (16)	0.0306 (8)
H6	0.3853	0.8322	0.8475	0.037*
C7	0.4965 (3)	0.6853 (3)	0.83628 (14)	0.0236 (7)
H7	0.5590	0.7233	0.8580	0.028*
C8	0.6459 (3)	0.6860 (3)	0.67581 (14)	0.0212 (6)
H8A	0.6363	0.7671	0.6971	0.025*
H8B	0.7037	0.7011	0.6474	0.025*
C9	0.5355 (2)	0.6548 (3)	0.64269 (13)	0.0192 (6)
C10	0.4343 (3)	0.7070 (4)	0.65835 (15)	0.0309 (8)
H10	0.4356	0.7684	0.6888	0.037*
C11	0.3307 (3)	0.6717 (5)	0.63062 (18)	0.0463 (11)
H11	0.2617	0.7076	0.6420	0.056*
C12	0.3303 (3)	0.5845 (5)	0.58683 (19)	0.0475 (11)
C13	0.4278 (3)	0.5319 (4)	0.56833 (16)	0.0375 (9)
H13	0.4253	0.4725	0.5370	0.045*
C14	0.5303 (3)	0.5679 (3)	0.59670 (14)	0.0249 (7)
H14	0.5988	0.5324	0.5845	0.030*
C15	0.8782 (2)	0.4800 (3)	0.71871 (13)	0.0187 (6)
H15A	0.9318	0.4967	0.7529	0.022*
H15B	0.8769	0.3867	0.7114	0.022*
C16	0.9180 (2)	0.5479 (3)	0.66665 (13)	0.0183 (6)
C17	0.8872 (3)	0.5034 (3)	0.61081 (14)	0.0242 (7)
H17	0.8426	0.4280	0.6062	0.029*
C18	0.9200 (3)	0.5665 (3)	0.56162 (15)	0.0324 (8)
H18	0.8983	0.5354	0.5237	0.039*
C19	0.9847 (3)	0.6754 (3)	0.56939 (16)	0.0323 (8)
C20	1.0173 (3)	0.7237 (3)	0.62352 (16)	0.0287 (7)
H20	1.0617	0.7994	0.6277	0.034*
C21	0.9836 (2)	0.6587 (3)	0.67181 (14)	0.0222 (6)
H21	1.0058	0.6906	0.7095	0.027*
C22	0.6302 (2)	0.2774 (3)	0.68712 (12)	0.0163 (6)
C23	0.5386 (2)	0.2056 (3)	0.65075 (13)	0.0189 (6)
H23A	0.5114	0.2615	0.6180	0.023*
H23B	0.4738	0.1915	0.6751	0.023*
C24	0.6704 (3)	0.1026 (4)	0.56691 (15)	0.0166 (13)	0.631 (4)
C25	0.7999 (3)	0.0258 (5)	0.49474 (17)	0.0273 (10)	0.631 (4)
H25A	0.8750	−0.0103	0.5077	0.033*	0.631 (4)
H25B	0.8097	0.1187	0.4884	0.033*	0.631 (4)
C26	0.7582 (5)	−0.0356 (5)	0.4389 (2)	0.0273 (11)	0.631 (4)
H26A	0.8159	−0.0255	0.4100	0.033*	0.631 (4)
H26B	0.6878	0.0076	0.4234	0.033*	0.631 (4)
C27	0.7341 (5)	−0.1788 (5)	0.4475 (2)	0.0275 (14)	0.631 (4)
H27A	0.6973	−0.2150	0.4112	0.033*	0.631 (4)
H27B	0.8064	−0.2249	0.4566	0.033*	0.631 (4)
C28	0.6562 (5)	−0.1965 (5)	0.4974 (2)	0.0292 (11)	0.631 (4)
H28A	0.5804	−0.1607	0.4857	0.035*	0.631 (4)
H28B	0.6470	−0.2889	0.5050	0.035*	0.631 (4)
C29	0.7039 (3)	−0.1307 (4)	0.55303 (17)	0.0224 (9)	0.631 (4)
H29A	0.6506	−0.1411	0.5840	0.027*	0.631 (4)
H29B	0.7774	−0.1699	0.5666	0.027*	0.631 (4)
C24'	0.6478 (3)	0.1059 (6)	0.5589 (3)	0.029 (3)	0.369 (4)
C25'	0.7185 (5)	0.0395 (8)	0.4665 (3)	0.0273 (10)	0.37
H25C	0.7472	0.1285	0.4672	0.033*	0.369 (4)
H25D	0.6632	0.0302	0.4324	0.033*	0.369 (4)
C26'	0.8152 (7)	−0.0511 (8)	0.4610 (4)	0.0273 (11)	0.37
H26C	0.8744	−0.0349	0.4927	0.033*	0.369 (4)
H26D	0.8491	−0.0365	0.4235	0.033*	0.369 (4)
C27'	0.7748 (9)	−0.1904 (9)	0.4642 (4)	0.0275 (14)	0.37
H27C	0.7178	−0.2082	0.4315	0.033*	0.369 (4)
H27D	0.8398	−0.2491	0.4609	0.033*	0.369 (4)
C28'	0.7223 (7)	−0.2116 (8)	0.5220 (4)	0.0292 (11)	0.37
H28C	0.6947	−0.3007	0.5244	0.035*	0.369 (4)
H28D	0.7801	−0.1972	0.5546	0.035*	0.369 (4)
C29'	0.6248 (5)	−0.1199 (6)	0.5267 (3)	0.0224 (9)	0.37
H29C	0.5644	−0.1395	0.4959	0.027*	0.369 (4)
H29D	0.5925	−0.1308	0.5649	0.027*	0.369 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01313 (9)	0.01198 (9)	0.01910 (10)	0.00144 (8)	0.00059 (7)	0.00057 (8)
S1	0.0223 (3)	0.0147 (3)	0.0196 (4)	−0.0040 (3)	0.0021 (3)	−0.0018 (3)
S2	0.0371 (4)	0.0163 (4)	0.0304 (5)	−0.0072 (3)	0.0054 (4)	0.0006 (3)
F1	0.0236 (10)	0.0570 (15)	0.0692 (16)	0.0201 (10)	0.0158 (10)	0.0259 (13)
F2	0.0422 (14)	0.109 (2)	0.076 (2)	−0.0369 (16)	−0.0362 (13)	0.0325 (18)
F3	0.0663 (16)	0.0503 (14)	0.0387 (13)	−0.0086 (12)	0.0230 (12)	0.0114 (11)
O1	0.0226 (11)	0.0145 (10)	0.0276 (12)	0.0009 (8)	−0.0042 (9)	−0.0019 (9)
O2	0.0204 (10)	0.0144 (10)	0.0238 (11)	−0.0009 (8)	−0.0049 (8)	0.0033 (9)
N1	0.029 (2)	0.0191 (16)	0.018 (2)	−0.0064 (18)	0.0059 (16)	−0.0010 (15)
N1'	0.029 (2)	0.0191 (16)	0.018 (2)	−0.0064 (18)	0.0059 (16)	−0.0010 (15)
C1	0.0197 (14)	0.0210 (14)	0.0204 (15)	−0.0020 (11)	0.0023 (12)	0.0036 (12)
C2	0.0194 (14)	0.0190 (15)	0.0200 (15)	−0.0025 (11)	0.0038 (11)	0.0052 (12)
C3	0.0199 (15)	0.0256 (16)	0.0275 (17)	−0.0024 (12)	0.0013 (13)	0.0032 (13)
C4	0.0148 (15)	0.046 (2)	0.034 (2)	−0.0019 (14)	0.0005 (13)	0.0118 (16)
C5	0.0184 (15)	0.038 (2)	0.040 (2)	0.0098 (14)	0.0113 (14)	0.0173 (16)
C6	0.0315 (18)	0.0217 (16)	0.041 (2)	0.0036 (13)	0.0173 (16)	0.0063 (15)
C7	0.0202 (15)	0.0235 (16)	0.0282 (17)	−0.0050 (12)	0.0091 (13)	0.0018 (13)
C8	0.0239 (15)	0.0146 (14)	0.0244 (16)	0.0028 (12)	−0.0032 (12)	0.0069 (12)
C9	0.0203 (14)	0.0169 (14)	0.0201 (15)	0.0011 (11)	−0.0004 (12)	0.0063 (12)
C10	0.0258 (16)	0.039 (2)	0.0282 (18)	0.0087 (15)	0.0018 (14)	0.0041 (15)
C11	0.0193 (17)	0.074 (3)	0.046 (2)	0.0072 (18)	−0.0001 (16)	0.018 (2)
C12	0.0280 (19)	0.068 (3)	0.044 (2)	−0.0182 (19)	−0.0180 (17)	0.022 (2)
C13	0.050 (2)	0.033 (2)	0.0270 (18)	−0.0134 (18)	−0.0155 (16)	0.0071 (16)
C14	0.0317 (17)	0.0224 (17)	0.0198 (16)	0.0013 (13)	−0.0029 (13)	0.0035 (12)
C15	0.0153 (13)	0.0154 (15)	0.0257 (16)	0.0013 (11)	0.0031 (11)	−0.0023 (12)
C16	0.0139 (12)	0.0161 (13)	0.0251 (15)	0.0020 (11)	0.0029 (11)	−0.0029 (12)
C17	0.0246 (15)	0.0193 (14)	0.0286 (17)	−0.0020 (12)	0.0016 (13)	−0.0034 (13)
C18	0.0383 (19)	0.034 (2)	0.0250 (18)	−0.0007 (15)	0.0039 (15)	−0.0038 (15)
C19	0.0365 (19)	0.0315 (19)	0.0306 (19)	0.0003 (15)	0.0145 (15)	0.0069 (15)
C20	0.0232 (16)	0.0233 (16)	0.041 (2)	−0.0021 (13)	0.0110 (14)	0.0004 (15)
C21	0.0175 (14)	0.0209 (15)	0.0284 (17)	−0.0005 (12)	0.0036 (12)	−0.0066 (13)
C22	0.0183 (13)	0.0146 (14)	0.0162 (14)	0.0004 (11)	0.0016 (11)	−0.0016 (11)
C23	0.0197 (14)	0.0130 (14)	0.0237 (16)	0.0012 (11)	−0.0007 (12)	−0.0037 (12)
C24	0.025 (3)	0.014 (3)	0.012 (3)	−0.007 (2)	0.004 (2)	−0.001 (2)
C25	0.031 (2)	0.026 (2)	0.026 (2)	−0.007 (2)	0.0096 (17)	−0.001 (2)
C26	0.033 (3)	0.033 (2)	0.016 (3)	−0.006 (3)	0.0051 (18)	−0.002 (2)
C27	0.029 (4)	0.032 (2)	0.022 (3)	−0.007 (3)	0.001 (2)	−0.009 (2)
C28	0.035 (3)	0.025 (2)	0.028 (3)	−0.011 (2)	0.010 (2)	−0.007 (2)
C29	0.033 (2)	0.018 (2)	0.017 (2)	−0.0037 (19)	0.0049 (16)	−0.0008 (17)
C24'	0.034 (6)	0.023 (7)	0.030 (7)	−0.003 (5)	−0.006 (5)	−0.001 (5)
C25'	0.031 (2)	0.026 (2)	0.026 (2)	−0.007 (2)	0.0096 (17)	−0.001 (2)
C26'	0.033 (3)	0.033 (2)	0.016 (3)	−0.006 (3)	0.0051 (18)	−0.002 (2)
C27'	0.029 (4)	0.032 (2)	0.022 (3)	−0.007 (3)	0.001 (2)	−0.009 (2)
C28'	0.035 (3)	0.025 (2)	0.028 (3)	−0.011 (2)	0.010 (2)	−0.007 (2)
C29'	0.033 (2)	0.018 (2)	0.017 (2)	−0.0037 (19)	0.0049 (16)	−0.0008 (17)

Geometric parameters (Å, º) top

Sn1—C1	2.144 (3)	C13—H13	0.9500
Sn1—C8	2.155 (3)	C14—H14	0.9500
Sn1—C15	2.158 (3)	C15—C16	1.498 (4)
Sn1—O1	2.175 (2)	C15—H15A	0.9900
Sn1—O2ⁱ	2.339 (2)	C15—H15B	0.9900
S1—C24'	1.793 (7)	C16—C17	1.392 (4)
S1—C23	1.792 (3)	C16—C21	1.394 (4)
S1—C24	1.796 (5)	C17—C18	1.390 (5)
S2—C24'	1.659 (7)	C17—H17	0.9500
S2—C24	1.662 (5)	C18—C19	1.376 (5)
F1—C5	1.369 (4)	C18—H18	0.9500
F2—C12	1.362 (4)	C19—C20	1.375 (5)
F3—C19	1.358 (4)	C20—C21	1.385 (5)
O1—C22	1.268 (3)	C20—H20	0.9500
O2—C22	1.241 (3)	C21—H21	0.9500
O2—Sn1ⁱⁱ	2.339 (2)	C22—C23	1.518 (4)
N1—C24	1.333 (6)	C23—H23A	0.9900
N1—C29	1.468 (5)	C23—H23B	0.9900
N1—C25	1.485 (5)	C25—C26	1.490 (6)
N1'—C24'	1.332 (8)	C25—H25A	0.9900
N1'—C29'	1.468 (7)	C25—H25B	0.9900
N1'—C25'	1.479 (7)	C26—C27	1.540 (6)
C1—C2	1.494 (4)	C26—H26A	0.9900
C1—H1A	0.9900	C26—H26B	0.9900
C1—H1B	0.9900	C27—C28	1.530 (6)
C2—C3	1.392 (4)	C27—H27A	0.9900
C2—C7	1.395 (4)	C27—H27B	0.9900
C3—C4	1.386 (4)	C28—C29	1.527 (6)
C3—H3	0.9500	C28—H28A	0.9900
C4—C5	1.369 (5)	C28—H28B	0.9900
C4—H4	0.9500	C29—H29A	0.9900
C5—C6	1.371 (5)	C29—H29B	0.9900
C6—C7	1.389 (4)	C25'—C26'	1.495 (8)
C6—H6	0.9500	C25'—H25C	0.9900
C7—H7	0.9500	C25'—H25D	0.9900
C8—C9	1.499 (4)	C26'—C27'	1.535 (9)
C8—H8A	0.9900	C26'—H26C	0.9900
C8—H8B	0.9900	C26'—H26D	0.9900
C9—C10	1.384 (4)	C27'—C28'	1.525 (8)
C9—C14	1.394 (4)	C27'—H27C	0.9900
C10—C11	1.389 (5)	C27'—H27D	0.9900
C10—H10	0.9500	C28'—C29'	1.507 (8)
C11—C12	1.359 (6)	C28'—H28C	0.9900
C11—H11	0.9500	C28'—H28D	0.9900
C12—C13	1.370 (6)	C29'—H29C	0.9900
C13—C14	1.386 (5)	C29'—H29D	0.9900

C1—Sn1—C8	120.72 (12)	F3—C19—C18	118.8 (3)
C1—Sn1—C15	126.65 (11)	C20—C19—C18	122.6 (3)
C8—Sn1—C15	111.80 (12)	C19—C20—C21	118.1 (3)
C1—Sn1—O1	90.56 (10)	C19—C20—H20	121.0
C8—Sn1—O1	90.20 (10)	C21—C20—H20	121.0
C15—Sn1—O1	98.28 (10)	C20—C21—C16	121.9 (3)
C1—Sn1—O2ⁱ	88.16 (10)	C20—C21—H21	119.1
C8—Sn1—O2ⁱ	82.46 (10)	C16—C21—H21	119.1
C15—Sn1—O2ⁱ	89.94 (9)	O2—C22—O1	123.7 (3)
O1—Sn1—O2ⁱ	170.59 (7)	O2—C22—C23	122.8 (3)
C24'—S1—C23	100.5 (2)	O1—C22—C23	113.3 (2)
C23—S1—C24	101.60 (18)	C22—C23—S1	117.0 (2)
C22—O1—Sn1	129.16 (19)	C22—C23—H23A	108.0
C22—O2—Sn1ⁱⁱ	151.17 (19)	S1—C23—H23A	108.0
C24—N1—C29	125.9 (4)	C22—C23—H23B	108.0
C24—N1—C25	122.3 (4)	S1—C23—H23B	108.0
C29—N1—C25	111.8 (4)	H23A—C23—H23B	107.3
C24'—N1'—C29'	125.0 (5)	N1—C24—S2	125.3 (3)
C24'—N1'—C25'	120.6 (6)	N1—C24—S1	114.2 (3)
C29'—N1'—C25'	114.5 (5)	S2—C24—S1	120.5 (3)
C2—C1—Sn1	110.7 (2)	N1—C25—C26	111.6 (3)
C2—C1—H1A	109.5	N1—C25—H25A	109.3
Sn1—C1—H1A	109.5	C26—C25—H25A	109.3
C2—C1—H1B	109.5	N1—C25—H25B	109.3
Sn1—C1—H1B	109.5	C26—C25—H25B	109.3
H1A—C1—H1B	108.1	H25A—C25—H25B	108.0
C3—C2—C7	117.9 (3)	C25—C26—C27	111.1 (4)
C3—C2—C1	121.5 (3)	C25—C26—H26A	109.4
C7—C2—C1	120.5 (3)	C27—C26—H26A	109.4
C4—C3—C2	121.4 (3)	C25—C26—H26B	109.4
C4—C3—H3	119.3	C27—C26—H26B	109.4
C2—C3—H3	119.3	H26A—C26—H26B	108.0
C5—C4—C3	118.3 (3)	C28—C27—C26	109.9 (4)
C5—C4—H4	120.9	C28—C27—H27A	109.7
C3—C4—H4	120.9	C26—C27—H27A	109.7
C4—C5—F1	118.5 (3)	C28—C27—H27B	109.7
C4—C5—C6	123.0 (3)	C26—C27—H27B	109.7
F1—C5—C6	118.5 (3)	H27A—C27—H27B	108.2
C5—C6—C7	117.8 (3)	C29—C28—C27	111.7 (4)
C5—C6—H6	121.1	C29—C28—H28A	109.3
C7—C6—H6	121.1	C27—C28—H28A	109.3
C6—C7—C2	121.5 (3)	C29—C28—H28B	109.3
C6—C7—H7	119.2	C27—C28—H28B	109.3
C2—C7—H7	119.2	H28A—C28—H28B	107.9
C9—C8—Sn1	116.0 (2)	N1—C29—C28	108.8 (3)
C9—C8—H8A	108.3	N1—C29—H29A	109.9
Sn1—C8—H8A	108.3	C28—C29—H29A	109.9
C9—C8—H8B	108.3	N1—C29—H29B	109.9
Sn1—C8—H8B	108.3	C28—C29—H29B	109.9
H8A—C8—H8B	107.4	H29A—C29—H29B	108.3
C10—C9—C14	117.6 (3)	N1'—C24'—S2	125.5 (5)
C10—C9—C8	121.1 (3)	N1'—C24'—S1	113.6 (5)
C14—C9—C8	121.2 (3)	S2—C24'—S1	120.9 (4)
C9—C10—C11	121.5 (4)	N1'—C25'—C26'	110.2 (5)
C9—C10—H10	119.2	N1'—C25'—H25C	109.6
C11—C10—H10	119.2	C26'—C25'—H25C	109.6
C12—C11—C10	118.5 (4)	N1'—C25'—H25D	109.6
C12—C11—H11	120.8	C26'—C25'—H25D	109.6
C10—C11—H11	120.8	H25C—C25'—H25D	108.1
C11—C12—F2	119.1 (4)	C25'—C26'—C27'	110.9 (8)
C11—C12—C13	122.8 (3)	C25'—C26'—H26C	109.5
F2—C12—C13	118.1 (4)	C27'—C26'—H26C	109.5
C12—C13—C14	117.9 (4)	C25'—C26'—H26D	109.5
C12—C13—H13	121.0	C27'—C26'—H26D	109.5
C14—C13—H13	121.0	H26C—C26'—H26D	108.1
C13—C14—C9	121.7 (3)	C28'—C27'—C26'	109.0 (8)
C13—C14—H14	119.2	C28'—C27'—H27C	109.9
C9—C14—H14	119.2	C26'—C27'—H27C	109.9
C16—C15—Sn1	110.79 (19)	C28'—C27'—H27D	109.9
C16—C15—H15A	109.5	C26'—C27'—H27D	109.9
Sn1—C15—H15A	109.5	H27C—C27'—H27D	108.3
C16—C15—H15B	109.5	C29'—C28'—C27'	109.2 (8)
Sn1—C15—H15B	109.5	C29'—C28'—H28C	109.8
H15A—C15—H15B	108.1	C27'—C28'—H28C	109.8
C17—C16—C21	117.7 (3)	C29'—C28'—H28D	109.8
C17—C16—C15	120.3 (3)	C27'—C28'—H28D	109.8
C21—C16—C15	122.0 (3)	H28C—C28'—H28D	108.3
C18—C17—C16	121.7 (3)	N1'—C29'—C28'	111.2 (5)
C18—C17—H17	119.2	N1'—C29'—H29C	109.4
C16—C17—H17	119.2	C28'—C29'—H29C	109.4
C19—C18—C17	118.1 (3)	N1'—C29'—H29D	109.4
C19—C18—H18	121.0	C28'—C29'—H29D	109.4
C17—C18—H18	121.0	H29C—C29'—H29D	108.0
F3—C19—C20	118.6 (3)

C1—Sn1—O1—C22	−83.6 (3)	C19—C20—C21—C16	−0.3 (5)
C8—Sn1—O1—C22	155.7 (3)	C17—C16—C21—C20	0.2 (4)
C15—Sn1—O1—C22	43.6 (3)	C15—C16—C21—C20	−177.9 (3)
C8—Sn1—C1—C2	10.2 (3)	Sn1ⁱⁱ—O2—C22—O1	149.7 (3)
C15—Sn1—C1—C2	178.85 (19)	Sn1ⁱⁱ—O2—C22—C23	−26.1 (6)
O1—Sn1—C1—C2	−80.4 (2)	Sn1—O1—C22—O2	0.8 (4)
O2ⁱ—Sn1—C1—C2	90.3 (2)	Sn1—O1—C22—C23	177.03 (18)
Sn1—C1—C2—C3	82.4 (3)	O2—C22—C23—S1	−27.3 (4)
Sn1—C1—C2—C7	−94.3 (3)	O1—C22—C23—S1	156.4 (2)
C7—C2—C3—C4	0.6 (5)	C24'—S1—C23—C22	−80.7 (2)
C1—C2—C3—C4	−176.3 (3)	C24—S1—C23—C22	−70.5 (2)
C2—C3—C4—C5	1.3 (5)	C29—N1—C24—S2	−179.80 (10)
C3—C4—C5—F1	177.8 (3)	C25—N1—C24—S2	0.15 (17)
C3—C4—C5—C6	−2.2 (5)	C29—N1—C24—S1	0.16 (15)
C4—C5—C6—C7	1.2 (5)	C25—N1—C24—S1	−179.89 (8)
F1—C5—C6—C7	−178.9 (3)	C24'—S2—C24—N1	100.1 (16)
C5—C6—C7—C2	0.9 (5)	C24'—S2—C24—S1	−79.9 (16)
C3—C2—C7—C6	−1.7 (4)	C24'—S1—C24—N1	−100.3 (15)
C1—C2—C7—C6	175.2 (3)	C23—S1—C24—N1	174.76 (15)
C1—Sn1—C8—C9	−67.4 (3)	C24'—S1—C24—S2	79.7 (15)
C15—Sn1—C8—C9	122.4 (2)	C23—S1—C24—S2	−5.27 (16)
O1—Sn1—C8—C9	23.4 (2)	C24—N1—C25—C26	−119.8 (4)
O2ⁱ—Sn1—C8—C9	−150.7 (2)	C29—N1—C25—C26	60.2 (4)
Sn1—C8—C9—C10	101.0 (3)	N1—C25—C26—C27	−55.1 (6)
Sn1—C8—C9—C14	−76.1 (3)	C25—C26—C27—C28	52.1 (6)
C14—C9—C10—C11	1.9 (5)	C26—C27—C28—C29	−53.8 (6)
C8—C9—C10—C11	−175.3 (3)	C24—N1—C29—C28	120.1 (4)
C9—C10—C11—C12	−0.6 (6)	C25—N1—C29—C28	−59.9 (3)
C10—C11—C12—F2	177.8 (4)	C27—C28—C29—N1	57.6 (5)
C10—C11—C12—C13	−1.1 (6)	C29'—N1'—C24'—S2	−179.98 (10)
C11—C12—C13—C14	1.4 (6)	C25'—N1'—C24'—S2	0.02 (17)
F2—C12—C13—C14	−177.6 (3)	C29'—N1'—C24'—S1	0.01 (15)
C12—C13—C14—C9	0.0 (5)	C25'—N1'—C24'—S1	−179.99 (8)
C10—C9—C14—C13	−1.6 (5)	C24—S2—C24'—N1'	−98.2 (16)
C8—C9—C14—C13	175.6 (3)	C24—S2—C24'—S1	81.8 (16)
C1—Sn1—C15—C16	−169.27 (19)	C23—S1—C24'—N1'	−164.49 (17)
C8—Sn1—C15—C16	0.3 (2)	C24—S1—C24'—N1'	98.5 (15)
O1—Sn1—C15—C16	93.8 (2)	C23—S1—C24'—S2	15.51 (17)
O2ⁱ—Sn1—C15—C16	−81.6 (2)	C24—S1—C24'—S2	−81.5 (15)
Sn1—C15—C16—C17	−84.4 (3)	C24'—N1'—C25'—C26'	125.9 (6)
Sn1—C15—C16—C21	93.6 (3)	C29'—N1'—C25'—C26'	−54.1 (6)
C21—C16—C17—C18	−0.1 (5)	N1'—C25'—C26'—C27'	55.3 (9)
C15—C16—C17—C18	178.0 (3)	C25'—C26'—C27'—C28'	−58.9 (10)
C16—C17—C18—C19	0.1 (5)	C26'—C27'—C28'—C29'	58.6 (10)
C17—C18—C19—F3	−179.7 (3)	C24'—N1'—C29'—C28'	−124.7 (6)
C17—C18—C19—C20	−0.3 (5)	C25'—N1'—C29'—C28'	55.3 (6)
F3—C19—C20—C21	179.8 (3)	C27'—C28'—C29'—N1'	−56.7 (9)
C18—C19—C20—C21	0.4 (5)

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

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₆F)₃(C₈H₁₂NO₂S₂)]
M_r	664.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.8016 (7), 10.4572 (6), 23.0334 (13)
β (°)	94.013 (1)
V (Å³)	2835.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.735, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	25437, 6498, 5328
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.077, 1.05
No. of reflections	6498
No. of parameters	371
No. of restraints	17
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −1.19

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	2.144 (3)	Sn1—O1	2.175 (2)
Sn1—C8	2.155 (3)	Sn1—O2ⁱ	2.339 (2)
Sn1—C15	2.158 (3)

O1—Sn1—O2ⁱ	170.59 (7)

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

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ng, S. W., Chen, W. & Kumar Das, V. G. (1989). J. Organomet. Chem. 346, 59–64. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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