[5-(4-Bromo-phenoxy-meth-yl)-1,3,4-thia-diazole-2-thiol-ato]triphenyl-tin(IV).

In title compound, [Sn(C(6)H(5))(3)(C(9)H(6)BrN(2)OS(2))], the Sn atom is five-coordinated and the 1,3,4-thia-diazole-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 intra-molecular C-H⋯N and inter-molecular 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); n class="Chemical">Ng et al. (1990); Rodarte de Moura et al. (1999).

Experimental

Crystal data

[Sn(n class="CellLine">C6H5)3(C9H6BrN2OS2)]

M = 652.18

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.077

S = 1.04

4610 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.38 e Å−3

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).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(C6H5)3(C9H6BrN2OS2)]	F(000) = 1288
Mr = 652.18	Dx = 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

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

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(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.003
4610 reflections	Δρmax = 0.54 e Å−3
308 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .