[5-(4-Bromo­phenoxy­meth­yl)-1,3,4-thia­diazole-2-thiol­ato]triphenyl­tin(IV)

Wang, Z.; Zhao, G.; Tian, L.

doi:10.1107/S1600536809012793

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m528

doi:10.1107/S1600536809012793

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[5-(4-Bromophenoxymethyl)-1,3,4-thiadiazole-2-thiolato]triphenyltin(IV)

Zhi-feng Wang,^a Gui-long Zhao ^b and Lai-jin Tian ^a ^*

^aSchool of Chemistry and Chemical Engineering, Qufu Normal University, Jining 273165, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: tianlaijin2009@yahoo.cn

(Received 1 April 2009; accepted 4 April 2009; online 18 April 2009)

In title compound, [Sn(C₆H₅)₃(C₉H₆BrN₂OS₂)], the Sn atom is five-coordinated and the 1,3,4-thiadiazole-2-thiol ligand acts as an S,N-bidentate chelating ligand. The five-coordinate Sn^IV atom forms four primary bonds, three to the phenyl groups and one to the S atom. Thus, the title complex has a distorted cis-trigonal bipyramidal geometry with the S atom and two C atoms occupying the equatorial plane, whereas the N atom and another C atom are in axial positions. In addition, there is a weak intramolecular Sn⋯N interaction. The crystal structure involves weak intramolecular C—H⋯N and intermolecular C—H⋯Br hydrogen bonding.

Related literature

For the biological activity of 1,3,4-thiadiazole compounds, see: Oruc et al. (2004); Sawhney & Sharma (1993); Srivastava & Pandey (1993). For the biological activity of organotin(IV) compounds, see: Jimenez-Perez et al. (2000). For related crystal structures, see: Ma et al. (2006); Ng et al. (1990); Rodarte de Moura et al. (1999).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₉H₆BrN₂OS₂)]
M_r = 652.18
Monoclinic, P 2₁ /n
a = 15.524 (3) Å
b = 9.766 (2) Å
c = 18.019 (4) Å
β = 107.10 (3)°
V = 2611.2 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.69 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.589, T_max = 0.673
17098 measured reflections
4610 independent reflections
3736 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.077
S = 1.04
4610 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C13	2.130 (3)
Sn1—C7	2.146 (3)
Sn1—C1	2.149 (3)
Sn1—S1	2.4721 (10)
Sn1⋯N1	2.919 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Br1ⁱ	0.93	2.87	3.627 (4)	139
C8—H8⋯N1	0.93	2.54	3.274 (5)	136
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012793/hg2497sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012793/hg2497Isup2.hkl

checkCIF report

Comment top

1, 3, 4-thiadiazole compounds, an important class of intermediates in the medical and chemical syntheses, have attracted pharmacologist's interest in recent years due to their biological activity, such as antibacterial, antiviral, growth regulation and antitumoural activity (Oruc et al., 2004; Sawhney & Sharma, 1993; Srivastava & Pandey, 1993). Meanwhile, organotins (IV) have been well known for their biological activities (Jimenez-Perez et al., 2000). In order to find a new compound with broad spectrum of bioactivity we have designed and synthesized the title compound.

The title compound, bond lengths and angles are normal and in a good agreement with those reported previously (Ma et al., 2006; Ng et al., 1990). The five coordinated tin atoms forms four primary bonds: three to the phenyl groups and one to the sulfur atom. In addition, there is a weak intramolecular Sn···N interaction, the Sn1···N1 bond length (2.92 (2) Å) is longer than the sum of covalent radii (2.15 Å), but is shorter than that reported in Ph₃Sn(MBZ) (3.07 Å) (Rodarte de Moura et al., 1999). So the ligand 1,3,4-thiadiazole-2-thiol acts as a bidentate S, N chelating ligand. The crystal structure involves weak intramolecular C—H···N and intermolecular C—H···Br hydrogen bonding.

Related literature top

Experimental top

5-[(4-Bromophenoxy)methyl]-2-mercapto-1,3,4-thiadiazole (0.31 g, 1 mmol) and Ph₃SnCl (0.385 g, 1 mmol) were dissolved in 30 ml of toluene, and the resultant mixture was heated to reflux for 6 h. The solvent was removed on a rotary evaporator, and the residue was heated in 50 ml of boiling dichloromethane/absolute ethanol (1/1 by volume). The solution was cooled to room temperature and then filtered, and the filtrate was evaporated slowly at room temperature, from which the crystals suitable for the X-ray diffraction were thus obtained.

Computing details top

Figures top

Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.

[5-(4-Bromophenoxymethyl)-1,3,4-thiadiazole-2-thiolato]triphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃(C₉H₆BrN₂OS₂)]	F(000) = 1288
M_r = 652.18	D_x = 1.659 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6604 reflections
a = 15.524 (3) Å	θ = 2.5–27.1°
b = 9.766 (2) Å	µ = 2.69 mm⁻¹
c = 18.019 (4) Å	T = 293 K
β = 107.10 (3)°	Platelet, colorless
V = 2611.2 (9) Å³	0.22 × 0.20 × 0.16 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4610 independent reflections
Radiation source: rotating anode	3736 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.034
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
ω and ϕ scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
T_min = 0.589, T_max = 0.673	l = −21→20
17098 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0416P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.003
4610 reflections	Δρ_max = 0.54 e Å⁻³
308 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (4)

Crystal data top

[Sn(C₆H₅)₃(C₉H₆BrN₂OS₂)]	V = 2611.2 (9) Å³
M_r = 652.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.524 (3) Å	µ = 2.69 mm⁻¹
b = 9.766 (2) Å	T = 293 K
c = 18.019 (4) Å	0.22 × 0.20 × 0.16 mm
β = 107.10 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4610 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3736 reflections with I > 2σ(I)
T_min = 0.589, T_max = 0.673	R_int = 0.034
17098 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	Δρ_max = 0.54 e Å⁻³
4610 reflections	Δρ_min = −0.38 e Å⁻³
308 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
Sn1	0.812768 (15)	0.08685 (2)	1.009453 (13)	0.04854 (12)
Br1	−0.04987 (3)	0.06136 (5)	0.59342 (3)	0.08367 (17)
S1	0.68434 (6)	0.19432 (11)	1.04208 (6)	0.0688 (3)
S2	0.49137 (6)	0.15741 (10)	0.93629 (6)	0.0633 (3)
O1	0.32794 (15)	0.1042 (2)	0.80766 (14)	0.0618 (6)
N1	0.62663 (18)	0.0247 (3)	0.92206 (17)	0.0562 (7)
N2	0.55438 (19)	−0.0210 (3)	0.86289 (18)	0.0596 (8)
C1	0.9210 (2)	0.1827 (3)	1.09675 (19)	0.0473 (8)
C2	0.9848 (2)	0.2580 (3)	1.0757 (2)	0.0584 (9)
H2	0.9786	0.2713	1.0232	0.070*
C3	1.0581 (2)	0.3144 (4)	1.1306 (2)	0.0705 (11)
H3	1.1003	0.3656	1.1150	0.085*
C4	1.0682 (3)	0.2949 (4)	1.2074 (2)	0.0729 (11)
H4	1.1177	0.3320	1.2444	0.088*
C5	1.0055 (3)	0.2207 (4)	1.2304 (2)	0.0775 (12)
H5	1.0124	0.2072	1.2829	0.093*
C6	0.9316 (3)	0.1658 (4)	1.1749 (2)	0.0674 (10)
H6	0.8887	0.1170	1.1906	0.081*
C7	0.8293 (2)	−0.1298 (3)	1.02802 (18)	0.0469 (8)
C8	0.7640 (3)	−0.2272 (3)	0.9964 (2)	0.0621 (9)
H8	0.7080	−0.2005	0.9642	0.075*
C9	0.7824 (3)	−0.3646 (4)	1.0128 (2)	0.0737 (11)
H9	0.7381	−0.4293	0.9914	0.088*
C10	0.8638 (3)	−0.4068 (4)	1.0595 (2)	0.0667 (10)
H10	0.8746	−0.4993	1.0705	0.080*
C11	0.9300 (2)	−0.3114 (4)	1.0904 (2)	0.0592 (9)
H11	0.9863	−0.3394	1.1214	0.071*
C12	0.9121 (2)	−0.1734 (4)	1.0750 (2)	0.0548 (9)
H12	0.9565	−0.1091	1.0968	0.066*
C13	0.8166 (2)	0.1580 (3)	0.89873 (19)	0.0475 (8)
C14	0.7985 (3)	0.2930 (4)	0.8760 (2)	0.0686 (10)
H14	0.7800	0.3537	0.9080	0.082*
C15	0.8078 (3)	0.3388 (4)	0.8055 (3)	0.0816 (13)
H15	0.7954	0.4296	0.7908	0.098*
C16	0.8350 (3)	0.2514 (5)	0.7582 (2)	0.0813 (13)
H16	0.8418	0.2824	0.7114	0.098*
C17	0.8521 (3)	0.1185 (5)	0.7795 (2)	0.0761 (11)
H17	0.8701	0.0584	0.7469	0.091*
C18	0.8431 (2)	0.0720 (3)	0.8490 (2)	0.0590 (9)
H18	0.8551	−0.0194	0.8625	0.071*
C19	0.6045 (2)	0.1174 (3)	0.9649 (2)	0.0571 (9)
C20	0.4795 (2)	0.0390 (3)	0.8630 (2)	0.0541 (9)
C21	0.3936 (2)	0.0089 (4)	0.8024 (2)	0.0681 (11)
H21A	0.4025	0.0140	0.7514	0.082*
H21B	0.3736	−0.0830	0.8095	0.082*
C22	0.2436 (2)	0.0887 (3)	0.7565 (2)	0.0503 (8)
C23	0.1754 (2)	0.1615 (3)	0.7739 (2)	0.0541 (9)
H23	0.1882	0.2155	0.8183	0.065*
C24	0.0885 (2)	0.1538 (3)	0.7253 (2)	0.0561 (9)
H24	0.0428	0.2034	0.7366	0.067*
C25	0.0695 (2)	0.0727 (3)	0.6602 (2)	0.0526 (9)
C26	0.1366 (2)	−0.0011 (4)	0.6430 (2)	0.0639 (10)
H26	0.1232	−0.0560	0.5989	0.077*
C27	0.2241 (2)	0.0064 (4)	0.6917 (2)	0.0615 (10)
H27	0.2696	−0.0440	0.6805	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04381 (17)	0.04862 (16)	0.04831 (17)	−0.00257 (11)	0.00596 (11)	−0.00390 (10)
Br1	0.0507 (3)	0.1201 (4)	0.0662 (3)	0.0068 (2)	−0.0046 (2)	0.0018 (2)
S1	0.0507 (6)	0.0825 (6)	0.0681 (6)	0.0058 (5)	0.0096 (5)	−0.0185 (5)
S2	0.0428 (5)	0.0659 (6)	0.0766 (7)	0.0112 (5)	0.0106 (5)	−0.0134 (5)
O1	0.0415 (14)	0.0626 (14)	0.0735 (17)	0.0067 (12)	0.0047 (12)	−0.0141 (13)
N1	0.0398 (16)	0.0599 (17)	0.0642 (19)	0.0036 (15)	0.0082 (15)	−0.0037 (15)
N2	0.0459 (18)	0.0541 (17)	0.075 (2)	0.0067 (15)	0.0116 (16)	−0.0043 (16)
C1	0.0456 (19)	0.0422 (17)	0.051 (2)	−0.0010 (16)	0.0094 (16)	−0.0037 (15)
C2	0.054 (2)	0.067 (2)	0.052 (2)	−0.0032 (19)	0.0142 (18)	−0.0060 (18)
C3	0.052 (2)	0.075 (3)	0.083 (3)	−0.016 (2)	0.018 (2)	−0.016 (2)
C4	0.064 (3)	0.069 (2)	0.073 (3)	−0.013 (2)	−0.001 (2)	−0.018 (2)
C5	0.104 (3)	0.072 (3)	0.044 (2)	−0.014 (3)	0.002 (2)	−0.006 (2)
C6	0.080 (3)	0.070 (2)	0.051 (2)	−0.024 (2)	0.016 (2)	−0.0039 (19)
C7	0.044 (2)	0.0523 (18)	0.0446 (19)	0.0023 (16)	0.0125 (16)	−0.0013 (15)
C8	0.049 (2)	0.052 (2)	0.073 (2)	−0.0048 (19)	−0.0012 (18)	−0.0059 (19)
C9	0.055 (2)	0.050 (2)	0.101 (3)	−0.002 (2)	−0.001 (2)	−0.005 (2)
C10	0.068 (3)	0.050 (2)	0.079 (3)	0.008 (2)	0.016 (2)	0.004 (2)
C11	0.043 (2)	0.069 (2)	0.063 (2)	0.017 (2)	0.0123 (18)	0.0032 (19)
C12	0.0399 (19)	0.061 (2)	0.060 (2)	0.0001 (18)	0.0101 (17)	−0.0073 (18)
C13	0.0360 (18)	0.0492 (18)	0.051 (2)	−0.0021 (15)	0.0031 (15)	−0.0020 (16)
C14	0.070 (3)	0.055 (2)	0.070 (3)	0.005 (2)	0.004 (2)	−0.001 (2)
C15	0.077 (3)	0.068 (3)	0.081 (3)	−0.011 (2)	−0.007 (2)	0.024 (2)
C16	0.069 (3)	0.112 (4)	0.055 (2)	−0.024 (3)	0.007 (2)	0.012 (3)
C17	0.071 (3)	0.098 (3)	0.063 (3)	−0.010 (3)	0.025 (2)	−0.009 (2)
C18	0.058 (2)	0.057 (2)	0.060 (2)	−0.0044 (18)	0.0140 (19)	0.0003 (18)
C19	0.048 (2)	0.058 (2)	0.060 (2)	0.0054 (18)	0.0094 (18)	−0.0035 (18)
C20	0.044 (2)	0.0504 (18)	0.064 (2)	0.0034 (17)	0.0102 (18)	−0.0033 (17)
C21	0.050 (2)	0.063 (2)	0.085 (3)	0.0012 (19)	0.011 (2)	−0.017 (2)
C22	0.0373 (18)	0.0498 (19)	0.059 (2)	−0.0015 (16)	0.0064 (16)	−0.0007 (17)
C23	0.048 (2)	0.0521 (19)	0.061 (2)	−0.0003 (17)	0.0152 (18)	−0.0091 (17)
C24	0.046 (2)	0.059 (2)	0.062 (2)	0.0056 (18)	0.0134 (18)	0.0024 (18)
C25	0.043 (2)	0.057 (2)	0.053 (2)	0.0025 (17)	0.0071 (17)	0.0107 (17)
C26	0.059 (2)	0.069 (2)	0.055 (2)	−0.002 (2)	0.0044 (19)	−0.0086 (19)
C27	0.046 (2)	0.069 (2)	0.065 (2)	0.0097 (19)	0.0092 (19)	−0.014 (2)

Geometric parameters (Å, º) top

Sn1—C13	2.130 (3)	C9—H9	0.9300
Sn1—C7	2.146 (3)	C10—C11	1.377 (5)
Sn1—C1	2.149 (3)	C10—H10	0.9300
Sn1—S1	2.4721 (10)	C11—C12	1.388 (5)
Sn1—N1	2.919 (3)	C11—H11	0.9300
Br1—C25	1.892 (4)	C12—H12	0.9300
S1—C19	1.738 (4)	C13—C18	1.376 (4)
S2—C19	1.724 (4)	C13—C14	1.384 (4)
S2—C20	1.725 (4)	C14—C15	1.393 (5)
O1—C22	1.370 (4)	C14—H14	0.9300
O1—C21	1.404 (4)	C15—C16	1.358 (6)
N1—C19	1.299 (4)	C15—H15	0.9300
N1—N2	1.375 (4)	C16—C17	1.357 (6)
N2—C20	1.301 (4)	C16—H16	0.9300
C1—C2	1.375 (4)	C17—C18	1.376 (5)
C1—C6	1.378 (4)	C17—H17	0.9300
C2—C3	1.384 (5)	C18—H18	0.9300
C2—H2	0.9300	C20—C21	1.485 (5)
C3—C4	1.360 (5)	C21—H21A	0.9700
C3—H3	0.9300	C21—H21B	0.9700
C4—C5	1.373 (5)	C22—C27	1.376 (5)
C4—H4	0.9300	C22—C23	1.386 (4)
C5—C6	1.389 (5)	C23—C24	1.376 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—H6	0.9300	C24—C25	1.375 (5)
C7—C12	1.382 (4)	C24—H24	0.9300
C7—C8	1.385 (5)	C25—C26	1.374 (5)
C8—C9	1.385 (5)	C26—C27	1.386 (5)
C8—H8	0.9300	C26—H26	0.9300
C9—C10	1.360 (5)	C27—H27	0.9300

C13—Sn1—C7	115.65 (11)	C18—C13—Sn1	120.5 (2)
C13—Sn1—C1	108.20 (12)	C14—C13—Sn1	121.9 (3)
C7—Sn1—C1	106.47 (12)	C13—C14—C15	120.6 (4)
C13—Sn1—S1	109.32 (9)	C13—C14—H14	119.7
C7—Sn1—S1	116.71 (8)	C15—C14—H14	119.7
C1—Sn1—S1	98.76 (9)	C16—C15—C14	120.3 (4)
C19—S1—Sn1	93.52 (12)	C16—C15—H15	119.8
C19—S2—C20	86.94 (17)	C14—C15—H15	119.8
C22—O1—C21	116.7 (3)	C17—C16—C15	119.6 (4)
C19—N1—N2	112.9 (3)	C17—C16—H16	120.2
C20—N2—N1	112.2 (3)	C15—C16—H16	120.2
C2—C1—C6	117.8 (3)	C16—C17—C18	120.7 (4)
C2—C1—Sn1	120.2 (2)	C16—C17—H17	119.7
C6—C1—Sn1	121.9 (2)	C18—C17—H17	119.7
C1—C2—C3	121.6 (3)	C17—C18—C13	121.3 (4)
C1—C2—H2	119.2	C17—C18—H18	119.3
C3—C2—H2	119.2	C13—C18—H18	119.3
C4—C3—C2	119.8 (4)	N1—C19—S2	113.8 (3)
C4—C3—H3	120.1	N1—C19—S1	121.7 (3)
C2—C3—H3	120.1	S2—C19—S1	124.4 (2)
C3—C4—C5	120.1 (4)	N2—C20—C21	121.3 (3)
C3—C4—H4	120.0	N2—C20—S2	114.1 (3)
C5—C4—H4	120.0	C21—C20—S2	124.5 (3)
C4—C5—C6	119.7 (3)	O1—C21—C20	109.4 (3)
C4—C5—H5	120.2	O1—C21—H21A	109.8
C6—C5—H5	120.2	C20—C21—H21A	109.8
C1—C6—C5	121.1 (3)	O1—C21—H21B	109.8
C1—C6—H6	119.5	C20—C21—H21B	109.8
C5—C6—H6	119.5	H21A—C21—H21B	108.2
C12—C7—C8	118.4 (3)	O1—C22—C27	124.3 (3)
C12—C7—Sn1	116.5 (2)	O1—C22—C23	115.7 (3)
C8—C7—Sn1	125.0 (3)	C27—C22—C23	120.0 (3)
C7—C8—C9	119.9 (4)	C24—C23—C22	120.0 (3)
C7—C8—H8	120.1	C24—C23—H23	120.0
C9—C8—H8	120.1	C22—C23—H23	120.0
C10—C9—C8	121.4 (4)	C25—C24—C23	119.9 (3)
C10—C9—H9	119.3	C25—C24—H24	120.0
C8—C9—H9	119.3	C23—C24—H24	120.0
C9—C10—C11	119.5 (3)	C26—C25—C24	120.5 (3)
C9—C10—H10	120.3	C26—C25—Br1	119.4 (3)
C11—C10—H10	120.3	C24—C25—Br1	120.1 (3)
C10—C11—C12	119.6 (3)	C25—C26—C27	119.8 (3)
C10—C11—H11	120.2	C25—C26—H26	120.1
C12—C11—H11	120.2	C27—C26—H26	120.1
C7—C12—C11	121.2 (3)	C22—C27—C26	119.8 (3)
C7—C12—H12	119.4	C22—C27—H27	120.1
C11—C12—H12	119.4	C26—C27—H27	120.1
C18—C13—C14	117.5 (3)

C13—Sn1—S1—C19	63.59 (15)	C1—Sn1—C13—C14	−66.9 (3)
C7—Sn1—S1—C19	−70.03 (16)	S1—Sn1—C13—C14	39.7 (3)
C1—Sn1—S1—C19	176.47 (15)	C18—C13—C14—C15	−0.6 (5)
C19—N1—N2—C20	0.0 (4)	Sn1—C13—C14—C15	175.4 (3)
C13—Sn1—C1—C2	−8.8 (3)	C13—C14—C15—C16	−0.1 (6)
C7—Sn1—C1—C2	116.1 (3)	C14—C15—C16—C17	0.7 (7)
S1—Sn1—C1—C2	−122.5 (3)	C15—C16—C17—C18	−0.7 (7)
C13—Sn1—C1—C6	174.5 (3)	C16—C17—C18—C13	0.0 (6)
C7—Sn1—C1—C6	−60.6 (3)	C14—C13—C18—C17	0.6 (5)
S1—Sn1—C1—C6	60.8 (3)	Sn1—C13—C18—C17	−175.4 (3)
C6—C1—C2—C3	0.6 (5)	N2—N1—C19—S2	0.1 (4)
Sn1—C1—C2—C3	−176.3 (3)	N2—N1—C19—S1	−178.5 (2)
C1—C2—C3—C4	0.4 (6)	C20—S2—C19—N1	−0.1 (3)
C2—C3—C4—C5	−0.7 (6)	C20—S2—C19—S1	178.4 (3)
C3—C4—C5—C6	−0.1 (6)	Sn1—S1—C19—N1	7.6 (3)
C2—C1—C6—C5	−1.3 (6)	Sn1—S1—C19—S2	−170.8 (2)
Sn1—C1—C6—C5	175.4 (3)	N1—N2—C20—C21	177.7 (3)
C4—C5—C6—C1	1.1 (6)	N1—N2—C20—S2	−0.1 (4)
C13—Sn1—C7—C12	104.7 (2)	C19—S2—C20—N2	0.1 (3)
C1—Sn1—C7—C12	−15.5 (3)	C19—S2—C20—C21	−177.6 (3)
S1—Sn1—C7—C12	−124.6 (2)	C22—O1—C21—C20	−178.6 (3)
C13—Sn1—C7—C8	−75.0 (3)	N2—C20—C21—O1	−169.3 (3)
C1—Sn1—C7—C8	164.8 (3)	S2—C20—C21—O1	8.3 (5)
S1—Sn1—C7—C8	55.7 (3)	C21—O1—C22—C27	−14.0 (5)
C12—C7—C8—C9	0.6 (5)	C21—O1—C22—C23	165.3 (3)
Sn1—C7—C8—C9	−179.7 (3)	O1—C22—C23—C24	179.2 (3)
C7—C8—C9—C10	−0.2 (6)	C27—C22—C23—C24	−1.5 (5)
C8—C9—C10—C11	−0.9 (6)	C22—C23—C24—C25	0.8 (5)
C9—C10—C11—C12	1.6 (6)	C23—C24—C25—C26	0.1 (5)
C8—C7—C12—C11	0.1 (5)	C23—C24—C25—Br1	179.8 (2)
Sn1—C7—C12—C11	−179.6 (2)	C24—C25—C26—C27	−0.1 (5)
C10—C11—C12—C7	−1.2 (5)	Br1—C25—C26—C27	−179.9 (3)
C7—Sn1—C13—C18	−10.3 (3)	O1—C22—C27—C26	−179.3 (3)
C1—Sn1—C13—C18	109.0 (3)	C23—C22—C27—C26	1.4 (5)
S1—Sn1—C13—C18	−144.5 (3)	C25—C26—C27—C22	−0.6 (6)
C7—Sn1—C13—C14	173.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Br1ⁱ	0.93	2.87	3.627 (4)	139
C8—H8···N1	0.93	2.54	3.274 (5)	136

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₉H₆BrN₂OS₂)]
M_r	652.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	15.524 (3), 9.766 (2), 18.019 (4)
β (°)	107.10 (3)
V (Å³)	2611.2 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.69
Crystal size (mm)	0.22 × 0.20 × 0.16

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.589, 0.673
No. of measured, independent and observed [I > 2σ(I)] reflections	17098, 4610, 3736
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.077, 1.04
No. of reflections	4610
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.38

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—C13	2.130 (3)	Sn1—S1	2.4721 (10)
Sn1—C7	2.146 (3)	Sn1—N1	2.919 (3)
Sn1—C1	2.149 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Br1ⁱ	0.93	2.87	3.627 (4)	139.0
C8—H8···N1	0.93	2.54	3.274 (5)	136.2

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

References

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Volume 65| Part 5| May 2009| Page m528

doi:10.1107/S1600536809012793

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