catena-Poly[[tris­(4-fluoro­benz­yl)tin(IV)]{μ-[(N,N-diisopropylcar­bamo­thioyl)sulfanyl]acetato-κ2O:O′}]

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

doi:10.1107/S1600536810005933

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m314

doi:10.1107/S1600536810005933

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catena-Poly[[tris(4-fluorobenzyl)tin(IV)]{μ-[(N,N-diisopropylcarbamothioyl)sulfanyl]acetato-κ²O:O′}]

Thy Chun 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 10 February 2010; accepted 13 February 2010; online 20 February 2010)

In the title compound, [Sn(C₇H₆F)₃(C₉H₁₆NO₂S₂)]_n, the Sn atom is coordinated in a slightly distorted, trans-C₃SnO₂ trigonal-bipyramidal environment. Symmetry-related Sn atoms are bridged by diisopropyldithiocarbamoylacetato ligands, forming a one-dimensional polymer along [001].

Related literature

Trialkyltin carboxylates are generally carboxylate-bridged polymers; see: Ng et al. (1988 ). For the direct synthesis of substituted tribenzyltin chlorides, see: Sisido et al. (1961 ). For the synthesis of dithiocarbamoylacetic acids, see: Nachmias (1952 ). For background to the triorganotin derivatives of dithiocarbamylacetic acids, see: Ng & Kumar Das (1991 ).

Experimental

Crystal data

[Sn(C₇H₆F)₃(C₉H₁₆NO₂S₂)]
M_r = 680.39
Monoclinic, P 2₁ /c
a = 11.2496 (2) Å
b = 25.7598 (5) Å
c = 11.4216 (2) Å
β = 105.427 (1)°
V = 3190.58 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.759, T_max = 0.909
21159 measured reflections
7090 independent reflections
5217 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.159
S = 1.09
7090 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 1.27 e Å⁻³
Δρ_min = −1.18 e Å⁻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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005933/lh2996sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005933/lh2996Isup2.hkl

checkCIF report

Comment top

Part of the one-dimensional polymer of the title compound is shown in Fig. 1.

Related literature top

Trialkyltin carboxylates are generally carboxylate-bridged polymers; see: Ng et al. (1988). For the direct synthesis of substituted tribenzyltin chlorides, see: Sisido et al. (1961). For the synthesis of dithiocarbamoylacetic acids, see: Nachmias (1952). For background to the triorganotin derivatives of dithiocarbamylacetic acids, see: Ng & Kumar Das (1991).

Experimental top

Diisopropyldithiocarbomylacetic acid was synthesized from diisopropylamine, carbon disulfide and chloroacetic acid (Nachmias, 1952). Tri(p-fluorobenzyl)tin chloride was prepared by direct synthesis from p-fluorobenzyl chloride and tin powder in a mixture of toluene and water (Sisido et al., 1961). The triorganotin chloride was hydrolyzed with dilute sodium hydroxide solution to give tri(p-fluorobenzyl)tin hydroxide. The carboxylic acid (0.10 g, 0.43 mmol) and the organotin hydroxide (0.20 g, 0.43 mmol) were heated in ethanol (100 ml) for 1 hour. After filtering the mixture, colorless crystals were obtained upon slow evaporation of the filtrate.

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(C₇H₆F)₃(C₉H₁₆N₂O₂S₂) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius [symmetry code: (i) x, -y+1/2, z+1/2].

catena-Poly[[tris(4-fluorobenzyl)tin(IV)]{µ-[(N,N- diisopropylcarbamothioyl)sulfanyl]acetato-κ²O:O'}] top

Crystal data top

[Sn(C₇H₆F)₃(C₉H₁₆NO₂S₂)]	F(000) = 1384
M_r = 680.39	D_x = 1.416 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5664 reflections
a = 11.2496 (2) Å	θ = 2.4–28.3°
b = 25.7598 (5) Å	µ = 0.98 mm⁻¹
c = 11.4216 (2) Å	T = 293 K
β = 105.427 (1)°	Block, colorless
V = 3190.58 (10) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	7090 independent reflections
Radiation source: fine-focus sealed tube	5217 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.759, T_max = 0.909	k = −31→33
21159 measured reflections	l = −14→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0769P)² + 3.6716P] where P = (F_o² + 2F_c²)/3
7090 reflections	(Δ/σ)_max = 0.001
352 parameters	Δρ_max = 1.27 e Å⁻³
0 restraints	Δρ_min = −1.18 e Å⁻³

Crystal data top

[Sn(C₇H₆F)₃(C₉H₁₆NO₂S₂)]	V = 3190.58 (10) Å³
M_r = 680.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2496 (2) Å	µ = 0.98 mm⁻¹
b = 25.7598 (5) Å	T = 293 K
c = 11.4216 (2) Å	0.30 × 0.20 × 0.10 mm
β = 105.427 (1)°

Data collection top

Bruker SMART APEX diffractometer	7090 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5217 reflections with I > 2σ(I)
T_min = 0.759, T_max = 0.909	R_int = 0.050
21159 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.09	Δρ_max = 1.27 e Å⁻³
7090 reflections	Δρ_min = −1.18 e Å⁻³
352 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.66161 (3)	0.225810 (13)	0.57255 (3)	0.03172 (13)
S1	0.70901 (16)	0.42111 (6)	0.37053 (14)	0.0515 (4)
S2	0.45463 (17)	0.38461 (7)	0.35217 (17)	0.0594 (4)
F1	1.1949 (5)	0.1403 (3)	0.9730 (5)	0.131 (2)
F2	1.0347 (5)	0.05335 (19)	0.3995 (7)	0.123 (2)
F3	0.1222 (4)	0.1519 (2)	0.2507 (4)	0.0944 (15)
O1	0.6613 (4)	0.26909 (14)	0.3765 (3)	0.0399 (9)
O2	0.6790 (3)	0.32296 (14)	0.2303 (3)	0.0395 (8)
N1	0.5111 (5)	0.47966 (18)	0.2933 (4)	0.0499 (12)
C1	0.8474 (5)	0.2552 (2)	0.6297 (5)	0.0398 (12)
H1A	0.8777	0.2587	0.5581	0.048*
H1B	0.8444	0.2897	0.6626	0.048*
C2	0.9392 (5)	0.2243 (2)	0.7210 (5)	0.0379 (12)
C3	1.0029 (6)	0.1843 (3)	0.6852 (6)	0.0578 (17)
H3	0.9881	0.1760	0.6033	0.069*
C4	1.0897 (7)	0.1561 (3)	0.7722 (9)	0.081 (2)
H4	1.1329	0.1291	0.7485	0.097*
C5	1.1106 (6)	0.1685 (4)	0.8913 (7)	0.075 (2)
C6	1.0492 (6)	0.2071 (3)	0.9296 (6)	0.065 (2)
H6	1.0640	0.2148	1.0118	0.078*
C7	0.9642 (5)	0.2348 (3)	0.8437 (5)	0.0491 (15)
H7	0.9219	0.2617	0.8692	0.059*
C8	0.6182 (5)	0.1582 (2)	0.4614 (5)	0.0432 (13)
H8A	0.5695	0.1351	0.4969	0.052*
H8B	0.5676	0.1685	0.3821	0.052*
C9	0.7277 (5)	0.1289 (2)	0.4448 (5)	0.0434 (13)
C10	0.7677 (6)	0.1362 (2)	0.3425 (6)	0.0534 (15)
H10	0.7243	0.1586	0.2824	0.064*
C11	0.8708 (7)	0.1112 (3)	0.3262 (8)	0.070 (2)
H11	0.8977	0.1164	0.2568	0.084*
C12	0.9309 (7)	0.0787 (3)	0.4153 (10)	0.078 (2)
C13	0.8933 (8)	0.0695 (3)	0.5164 (8)	0.077 (2)
H13	0.9357	0.0460	0.5743	0.093*
C14	0.7925 (7)	0.0953 (3)	0.5329 (6)	0.0645 (19)
H14	0.7676	0.0901	0.6034	0.077*
C15	0.4941 (5)	0.2654 (2)	0.5752 (5)	0.0413 (13)
H15A	0.4839	0.2659	0.6569	0.050*
H15B	0.4962	0.3010	0.5478	0.050*
C16	0.3905 (5)	0.2365 (2)	0.4919 (5)	0.0384 (13)
C17	0.3326 (6)	0.1950 (3)	0.5316 (5)	0.0514 (15)
H17	0.3547	0.1861	0.6134	0.062*
C18	0.2426 (6)	0.1667 (3)	0.4506 (7)	0.0626 (18)
H18	0.2041	0.1391	0.4779	0.075*
C19	0.2107 (6)	0.1796 (3)	0.3309 (6)	0.0590 (17)
C20	0.2654 (6)	0.2200 (3)	0.2879 (6)	0.0579 (18)
H20	0.2435	0.2282	0.2057	0.070*
C21	0.3534 (5)	0.2481 (3)	0.3690 (5)	0.0484 (14)
H21	0.3898	0.2761	0.3404	0.058*
C22	0.6819 (5)	0.3121 (2)	0.3390 (5)	0.0356 (12)
C23	0.7238 (6)	0.3564 (2)	0.4291 (5)	0.0434 (13)
H23A	0.8099	0.3507	0.4709	0.052*
H23B	0.6776	0.3542	0.4895	0.052*
C24	0.5468 (6)	0.4321 (2)	0.3331 (5)	0.0438 (13)
C25	0.6014 (7)	0.5209 (2)	0.2852 (6)	0.0654 (19)
H25	0.6822	0.5091	0.3340	0.078*
C26	0.5775 (10)	0.5729 (3)	0.3367 (7)	0.104 (4)
H26A	0.5754	0.5686	0.4196	0.157*
H26B	0.4998	0.5864	0.2899	0.157*
H26C	0.6422	0.5967	0.3332	0.157*
C27	0.6113 (10)	0.5271 (3)	0.1567 (7)	0.092 (3)
H27A	0.6293	0.4940	0.1264	0.138*
H27B	0.6763	0.5511	0.1557	0.138*
H27C	0.5348	0.5400	0.1062	0.138*
C28	0.3806 (7)	0.4941 (3)	0.2433 (6)	0.0628 (18)
H28	0.3811	0.5291	0.2098	0.075*
C29	0.3171 (9)	0.4989 (4)	0.3436 (8)	0.106 (3)
H29A	0.2324	0.5084	0.3096	0.159*
H29B	0.3574	0.5251	0.4001	0.159*
H29C	0.3210	0.4663	0.3850	0.159*
C30	0.3161 (7)	0.4601 (3)	0.1383 (7)	0.078 (2)
H30A	0.3625	0.4597	0.0788	0.117*
H30B	0.2350	0.4736	0.1022	0.117*
H30C	0.3098	0.4255	0.1668	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0307 (2)	0.0347 (2)	0.02739 (18)	−0.00011 (16)	0.00355 (13)	−0.00373 (14)
S1	0.0613 (10)	0.0373 (8)	0.0522 (9)	0.0002 (7)	0.0088 (7)	−0.0025 (7)
S2	0.0637 (11)	0.0510 (10)	0.0694 (11)	0.0104 (8)	0.0281 (9)	0.0142 (8)
F1	0.084 (3)	0.184 (6)	0.113 (4)	0.071 (4)	0.003 (3)	0.070 (4)
F2	0.085 (3)	0.071 (3)	0.226 (7)	0.025 (3)	0.063 (4)	−0.010 (4)
F3	0.068 (3)	0.118 (4)	0.085 (3)	−0.044 (3)	0.001 (2)	−0.019 (3)
O1	0.048 (2)	0.036 (2)	0.0333 (19)	0.0021 (17)	0.0058 (16)	0.0027 (16)
O2	0.051 (2)	0.039 (2)	0.0285 (18)	0.0038 (18)	0.0116 (16)	−0.0028 (15)
N1	0.072 (4)	0.038 (3)	0.037 (2)	0.011 (3)	0.010 (2)	0.003 (2)
C1	0.031 (3)	0.050 (3)	0.037 (3)	−0.006 (3)	0.006 (2)	0.004 (2)
C2	0.027 (3)	0.050 (3)	0.034 (3)	−0.002 (2)	0.004 (2)	0.005 (2)
C3	0.056 (4)	0.063 (4)	0.053 (4)	0.008 (3)	0.013 (3)	−0.009 (3)
C4	0.064 (5)	0.068 (5)	0.105 (7)	0.031 (4)	0.012 (4)	0.001 (5)
C5	0.048 (4)	0.102 (6)	0.066 (5)	0.022 (4)	−0.001 (3)	0.034 (4)
C6	0.046 (4)	0.111 (6)	0.035 (3)	0.015 (4)	0.005 (3)	0.014 (4)
C7	0.035 (3)	0.073 (4)	0.036 (3)	0.006 (3)	0.004 (2)	−0.006 (3)
C8	0.043 (3)	0.043 (3)	0.043 (3)	−0.009 (3)	0.009 (2)	−0.014 (2)
C9	0.049 (3)	0.033 (3)	0.045 (3)	−0.007 (3)	0.008 (3)	−0.011 (2)
C10	0.060 (4)	0.040 (3)	0.063 (4)	0.003 (3)	0.021 (3)	0.002 (3)
C11	0.071 (5)	0.050 (4)	0.101 (6)	−0.001 (4)	0.044 (4)	−0.003 (4)
C12	0.051 (4)	0.039 (4)	0.143 (8)	0.010 (3)	0.021 (5)	−0.013 (5)
C13	0.085 (6)	0.041 (4)	0.092 (6)	0.020 (4)	0.001 (5)	0.001 (4)
C14	0.087 (5)	0.041 (4)	0.062 (4)	0.007 (4)	0.013 (4)	−0.001 (3)
C15	0.040 (3)	0.047 (3)	0.036 (3)	0.006 (3)	0.009 (2)	−0.002 (2)
C16	0.030 (3)	0.048 (3)	0.037 (3)	0.012 (2)	0.009 (2)	0.004 (2)
C17	0.049 (4)	0.064 (4)	0.043 (3)	0.003 (3)	0.015 (3)	0.010 (3)
C18	0.053 (4)	0.068 (5)	0.069 (5)	−0.013 (4)	0.019 (3)	0.011 (4)
C19	0.041 (3)	0.070 (5)	0.063 (4)	−0.011 (3)	0.009 (3)	−0.007 (4)
C20	0.040 (3)	0.088 (5)	0.039 (3)	−0.004 (3)	−0.003 (3)	0.003 (3)
C21	0.044 (3)	0.060 (4)	0.037 (3)	−0.008 (3)	0.004 (3)	0.007 (3)
C22	0.032 (3)	0.040 (3)	0.032 (3)	0.007 (2)	0.003 (2)	0.000 (2)
C23	0.052 (3)	0.041 (3)	0.032 (3)	0.007 (3)	0.002 (2)	−0.002 (2)
C24	0.065 (4)	0.036 (3)	0.032 (3)	0.003 (3)	0.016 (3)	−0.003 (2)
C25	0.093 (5)	0.037 (4)	0.056 (4)	−0.002 (4)	0.002 (4)	0.004 (3)
C26	0.179 (10)	0.046 (4)	0.062 (5)	0.012 (5)	−0.013 (6)	−0.010 (4)
C27	0.143 (8)	0.066 (5)	0.076 (5)	−0.024 (5)	0.044 (6)	0.006 (4)
C28	0.079 (5)	0.054 (4)	0.054 (4)	0.021 (4)	0.015 (3)	0.009 (3)
C29	0.133 (8)	0.113 (8)	0.085 (6)	0.074 (7)	0.050 (6)	0.019 (5)
C30	0.073 (5)	0.088 (6)	0.066 (5)	0.010 (4)	0.004 (4)	0.023 (4)

Geometric parameters (Å, º) top

Sn1—C8	2.133 (5)	C12—C13	1.352 (12)
Sn1—C15	2.151 (5)	C13—C14	1.369 (10)
Sn1—C1	2.155 (5)	C13—H13	0.9300
Sn1—O2ⁱ	2.162 (3)	C14—H14	0.9300
Sn1—O1	2.500 (4)	C15—C16	1.493 (8)
S1—C24	1.782 (6)	C15—H15A	0.9700
S1—C23	1.787 (6)	C15—H15B	0.9700
S2—C24	1.655 (6)	C16—C21	1.387 (8)
F1—C5	1.351 (8)	C16—C17	1.389 (8)
F2—C12	1.391 (8)	C17—C18	1.383 (9)
F3—C19	1.361 (7)	C17—H17	0.9300
O1—C22	1.232 (6)	C18—C19	1.359 (9)
O2—C22	1.265 (6)	C18—H18	0.9300
O2—Sn1ⁱⁱ	2.162 (3)	C19—C20	1.366 (9)
N1—C24	1.332 (7)	C20—C21	1.368 (8)
N1—C28	1.474 (8)	C20—H20	0.9300
N1—C25	1.490 (9)	C21—H21	0.9300
C1—C2	1.488 (7)	C22—C23	1.525 (7)
C1—H1A	0.9700	C23—H23A	0.9700
C1—H1B	0.9700	C23—H23B	0.9700
C2—C3	1.378 (8)	C25—C27	1.510 (10)
C2—C7	1.382 (8)	C25—C26	1.516 (10)
C3—C4	1.396 (10)	C25—H25	0.9800
C3—H3	0.9300	C26—H26A	0.9600
C4—C5	1.356 (11)	C26—H26B	0.9600
C4—H4	0.9300	C26—H26C	0.9600
C5—C6	1.349 (11)	C27—H27A	0.9600
C6—C7	1.373 (9)	C27—H27B	0.9600
C6—H6	0.9300	C27—H27C	0.9600
C7—H7	0.9300	C28—C30	1.506 (10)
C8—C9	1.500 (8)	C28—C29	1.508 (10)
C8—H8A	0.9700	C28—H28	0.9800
C8—H8B	0.9700	C29—H29A	0.9600
C9—C10	1.372 (8)	C29—H29B	0.9600
C9—C14	1.380 (9)	C29—H29C	0.9600
C10—C11	1.382 (9)	C30—H30A	0.9600
C10—H10	0.9300	C30—H30B	0.9600
C11—C12	1.351 (11)	C30—H30C	0.9600
C11—H11	0.9300

C8—Sn1—C15	109.5 (2)	Sn1—C15—H15B	110.3
C8—Sn1—C1	121.1 (2)	H15A—C15—H15B	108.6
C15—Sn1—C1	127.8 (2)	C21—C16—C17	117.0 (5)
C8—Sn1—O2ⁱ	88.72 (19)	C21—C16—C15	120.8 (5)
C15—Sn1—O2ⁱ	98.59 (18)	C17—C16—C15	122.1 (5)
C1—Sn1—O2ⁱ	94.94 (17)	C18—C17—C16	120.7 (6)
C8—Sn1—O1	83.41 (18)	C18—C17—H17	119.6
C15—Sn1—O1	90.48 (18)	C16—C17—H17	119.6
C1—Sn1—O1	83.39 (17)	C19—C18—C17	119.7 (6)
O2ⁱ—Sn1—O1	169.58 (13)	C19—C18—H18	120.2
C24—S1—C23	103.0 (3)	C17—C18—H18	120.2
C22—O1—Sn1	139.2 (3)	C18—C19—F3	120.0 (6)
C22—O2—Sn1ⁱⁱ	131.5 (3)	C18—C19—C20	121.6 (6)
C24—N1—C28	123.0 (6)	F3—C19—C20	118.4 (6)
C24—N1—C25	121.9 (6)	C21—C20—C19	118.3 (6)
C28—N1—C25	114.9 (5)	C21—C20—H20	120.9
C2—C1—Sn1	117.4 (4)	C19—C20—H20	120.9
C2—C1—H1A	107.9	C20—C21—C16	122.7 (6)
Sn1—C1—H1A	107.9	C20—C21—H21	118.6
C2—C1—H1B	107.9	C16—C21—H21	118.6
Sn1—C1—H1B	107.9	O1—C22—O2	125.6 (5)
H1A—C1—H1B	107.2	O1—C22—C23	119.4 (5)
C3—C2—C7	117.8 (5)	O2—C22—C23	114.8 (5)
C3—C2—C1	120.7 (5)	C22—C23—S1	117.6 (4)
C7—C2—C1	121.5 (5)	C22—C23—H23A	107.9
C2—C3—C4	119.8 (6)	S1—C23—H23A	107.9
C2—C3—H3	120.1	C22—C23—H23B	107.9
C4—C3—H3	120.1	S1—C23—H23B	107.9
C5—C4—C3	119.6 (7)	H23A—C23—H23B	107.2
C5—C4—H4	120.2	N1—C24—S2	125.6 (5)
C3—C4—H4	120.2	N1—C24—S1	115.1 (5)
C4—C5—F1	118.0 (8)	S2—C24—S1	119.3 (3)
C4—C5—C6	122.1 (6)	N1—C25—C27	111.3 (6)
F1—C5—C6	119.9 (7)	N1—C25—C26	114.3 (7)
C5—C6—C7	118.1 (6)	C27—C25—C26	110.5 (6)
C5—C6—H6	120.9	N1—C25—H25	106.7
C7—C6—H6	120.9	C27—C25—H25	106.7
C6—C7—C2	122.5 (6)	C26—C25—H25	106.7
C6—C7—H7	118.8	C25—C26—H26A	109.5
C2—C7—H7	118.8	C25—C26—H26B	109.5
C9—C8—Sn1	114.9 (4)	H26A—C26—H26B	109.5
C9—C8—H8A	108.5	C25—C26—H26C	109.5
Sn1—C8—H8A	108.5	H26A—C26—H26C	109.5
C9—C8—H8B	108.5	H26B—C26—H26C	109.5
Sn1—C8—H8B	108.5	C25—C27—H27A	109.5
H8A—C8—H8B	107.5	C25—C27—H27B	109.5
C10—C9—C14	118.6 (6)	H27A—C27—H27B	109.5
C10—C9—C8	120.3 (6)	C25—C27—H27C	109.5
C14—C9—C8	121.1 (6)	H27A—C27—H27C	109.5
C9—C10—C11	121.9 (7)	H27B—C27—H27C	109.5
C9—C10—H10	119.1	N1—C28—C30	112.4 (6)
C11—C10—H10	119.1	N1—C28—C29	110.5 (6)
C12—C11—C10	117.2 (7)	C30—C28—C29	115.4 (8)
C12—C11—H11	121.4	N1—C28—H28	105.9
C10—C11—H11	121.4	C30—C28—H28	105.9
C11—C12—C13	123.0 (7)	C29—C28—H28	105.9
C11—C12—F2	117.5 (9)	C28—C29—H29A	109.5
C13—C12—F2	119.5 (8)	C28—C29—H29B	109.5
C12—C13—C14	119.4 (7)	H29A—C29—H29B	109.5
C12—C13—H13	120.3	C28—C29—H29C	109.5
C14—C13—H13	120.3	H29A—C29—H29C	109.5
C13—C14—C9	120.0 (7)	H29B—C29—H29C	109.5
C13—C14—H14	120.0	C28—C30—H30A	109.5
C9—C14—H14	120.0	C28—C30—H30B	109.5
C16—C15—Sn1	107.0 (3)	H30A—C30—H30B	109.5
C16—C15—H15A	110.3	C28—C30—H30C	109.5
Sn1—C15—H15A	110.3	H30A—C30—H30C	109.5
C16—C15—H15B	110.3	H30B—C30—H30C	109.5

C8—Sn1—O1—C22	−176.6 (5)	C1—Sn1—C15—C16	162.0 (3)
C15—Sn1—O1—C22	73.8 (5)	O2ⁱ—Sn1—C15—C16	−94.8 (4)
C1—Sn1—O1—C22	−54.2 (5)	O1—Sn1—C15—C16	80.0 (4)
O2ⁱ—Sn1—O1—C22	−135.5 (7)	Sn1—C15—C16—C21	−87.7 (6)
C8—Sn1—C1—C2	−70.7 (5)	Sn1—C15—C16—C17	88.0 (6)
C15—Sn1—C1—C2	125.7 (4)	C21—C16—C17—C18	0.2 (9)
O2ⁱ—Sn1—C1—C2	20.8 (4)	C15—C16—C17—C18	−175.6 (6)
O1—Sn1—C1—C2	−148.9 (4)	C16—C17—C18—C19	0.3 (10)
Sn1—C1—C2—C3	86.3 (6)	C17—C18—C19—F3	−180.0 (6)
Sn1—C1—C2—C7	−94.2 (6)	C17—C18—C19—C20	−0.1 (11)
C7—C2—C3—C4	−0.3 (10)	C18—C19—C20—C21	−0.6 (11)
C1—C2—C3—C4	179.2 (6)	F3—C19—C20—C21	179.3 (6)
C2—C3—C4—C5	0.0 (12)	C19—C20—C21—C16	1.2 (10)
C3—C4—C5—F1	179.7 (7)	C17—C16—C21—C20	−1.0 (9)
C3—C4—C5—C6	0.5 (13)	C15—C16—C21—C20	174.9 (6)
C4—C5—C6—C7	−0.8 (13)	Sn1—O1—C22—O2	177.0 (3)
F1—C5—C6—C7	−179.9 (7)	Sn1—O1—C22—C23	1.7 (8)
C5—C6—C7—C2	0.5 (11)	Sn1ⁱⁱ—O2—C22—O1	−8.5 (8)
C3—C2—C7—C6	0.0 (9)	Sn1ⁱⁱ—O2—C22—C23	166.9 (3)
C1—C2—C7—C6	−179.5 (6)	O1—C22—C23—S1	−162.0 (4)
C15—Sn1—C8—C9	176.0 (4)	O2—C22—C23—S1	22.3 (6)
C1—Sn1—C8—C9	9.6 (5)	C24—S1—C23—C22	72.4 (5)
O2ⁱ—Sn1—C8—C9	−85.4 (4)	C28—N1—C24—S2	−9.3 (8)
O1—Sn1—C8—C9	87.8 (4)	C25—N1—C24—S2	176.7 (4)
Sn1—C8—C9—C10	−97.9 (6)	C28—N1—C24—S1	171.9 (4)
Sn1—C8—C9—C14	80.2 (6)	C25—N1—C24—S1	−2.1 (7)
C14—C9—C10—C11	−0.4 (10)	C23—S1—C24—N1	176.2 (4)
C8—C9—C10—C11	177.7 (6)	C23—S1—C24—S2	−2.6 (4)
C9—C10—C11—C12	0.3 (11)	C24—N1—C25—C27	100.4 (7)
C10—C11—C12—C13	1.0 (12)	C28—N1—C25—C27	−74.0 (8)
C10—C11—C12—F2	180.0 (6)	C24—N1—C25—C26	−133.4 (6)
C11—C12—C13—C14	−2.2 (13)	C28—N1—C25—C26	52.1 (7)
F2—C12—C13—C14	178.8 (7)	C24—N1—C28—C30	−56.2 (8)
C12—C13—C14—C9	2.1 (12)	C25—N1—C28—C30	118.2 (7)
C10—C9—C14—C13	−0.8 (10)	C24—N1—C28—C29	74.3 (8)
C8—C9—C14—C13	−178.9 (6)	C25—N1—C28—C29	−111.4 (7)
C8—Sn1—C15—C16	−3.1 (4)

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

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₆F)₃(C₉H₁₆NO₂S₂)]
M_r	680.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.2496 (2), 25.7598 (5), 11.4216 (2)
β (°)	105.427 (1)
V (Å³)	3190.58 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
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	0.759, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	21159, 7090, 5217
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.159, 1.09
No. of reflections	7090
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.27, −1.18

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

Acknowledgements

We thank the University of Malaya (RG020/09AFR and PS338/2009C) for supporting this study.

References

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