Aqua­chlorido{2-[2-(cyclo­hexyl­carbamo­thioyl-κS)hydrazinyl­idene-κN1]propano­ato(2−)}phenyl­tin(IV)

Affan, M.A.; Salam, M.A.; Jusoh, I.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536810031715

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1112-m1113

https://doi.org/10.1107/S1600536810031715

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Aquachlorido{2-[2-(cyclohexylcarbamothioyl-κS)hydrazinylidene-κN¹]propanoato(2−)}phenyltin(IV)

Md. Abu Affan,^a ‡ Md. Abdus Salam,^a Ismail Jusoh,^a Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 4 August 2010; accepted 6 August 2010; online 18 August 2010)

In the title organotin compound, [Sn(C₆H₅)(C₁₀H₁₅N₃O₂S)Cl(H₂O)], the Sn atom is coordinated by the S, O, and imine N atoms of the dinegative tridentate ligand, a chloride ligand, the ipso-C atom of a phenyl ligand and by a water molecule in a distorted octahedral coordination environment. Coordinated water molecules link the organotin molecules by forming O—H⋯O hydrogen bonds with both carbonyl and carboxylate O atoms, leading to 12-membered {⋯OCO⋯HOH⋯}₂ synthons. This results in the formation of supramolecular chains along the c axis. The chains pack in the ac plane and stack along the b axis with links between layers afforded by N—H⋯Cl hydrogen bonds.

Related literature

For background to the biological activity of tin/organotin compounds, see: Gielen & Tiekink (2005 ). For related studies on organotin compounds, see: Affan et al. (2009 ); Zukerman-Schpector et al. (2009 ); Affan et al. (2010 ).

Experimental

Crystal data

[Sn(C₆H₅)(C₁₀H₁₅N₃O₂S)Cl(H₂O)]
M_r = 490.57
Monoclinic, C 2/c
a = 16.3904 (9) Å
b = 19.2018 (10) Å
c = 13.1127 (7) Å
β = 108.4421 (7)°
V = 3915.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.57 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 = 0.613, T_max = 0.746
18020 measured reflections
4498 independent reflections
3853 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.091
S = 1.19
4498 reflections
239 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn—C11	2.123 (3)
Sn—O1	2.148 (2)
Sn—N3	2.195 (3)
Sn—O1w	2.224 (2)
Sn—Cl1	2.4524 (8)
Sn—S1	2.4598 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯O1ⁱ	0.84 (5)	1.94 (3)	2.733 (3)	159 (6)
O1w—H2w⋯O2ⁱⁱ	0.83 (5)	1.81 (2)	2.645 (3)	174 (5)
N1—H1n⋯Cl1ⁱⁱⁱ	0.86 (3)	2.59 (2)	3.407 (3)	161 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810031715/lh5114sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031715/lh5114Isup2.hkl

checkCIF report

Comment top

Organotin compounds continue to attract considerable owing to the wide variety of biological properties (Gielen & Tiekink, 2005). In continuation of our work in this area (Affan et al., 2009; Zukerman-Schpector et al., 2009; Affan et al. 2010), the title organotin compound, (I), was synthesized and structurally characterized.

The Sn atom is coordinated via the S, O, and imine-N atoms of the dinegative tridentate ligand, thereby forming two planar five-membered chelate rings. The distorted CClNO₂S octahedral coordination geometry is completed by an aqua ligand, a chloride atom, and the ipso-C atom of the phenyl group, Table 1. The greatest distortion from the ideal octahedral geometry is found in the O1–Sn–S1 angle of 153.73 (6) °, a feature which arises due to the restricted bite distances of the chelate rings.

The most notable feature of the crystal packing is the formation of O–H···O and N–H···Cl hydrogen bonds, Table 1. The water molecule hydrogen bonds to a carbonyl-O of one molecule and a carboxyl-O of another. Two-fold symmetry leads to the formation of a 12-membered {···OCO···HOH···}₂ synthon and the formation of a supramolecular chain along the c axis, Fig. 2. The chains pack in the ac plane and stack along the b axis with the primary interactions between successive layers being hydrogen bonds of the type N–H···Cl, Fig. 3.

Related literature top

For background to the biological activity of tin/organotin compounds, see: Gielen & Tiekink (2005). For related studies on organotin compounds, see: Affan et al. (2009); Zukerman-Schpector et al. (2009); Affan et al. (2010).

Experimental top

The pyruvic acid cyclohexyl thiosemicarbazone ligand (0.243 g, 1.0 mmol) was dissolved in dry methanol (10 ml) in a Schlenk apparatus under a purified dry nitrogen atmosphere. Phenyltin(IV) trichloride (0.302 g, 1.0 mmol) dissolved in absolute methanol (10 ml) was added drop-wise. The resulting mixture was refluxed for 5 h. The resulting solid was filtered and dried in vacuo over silica gel. Re-crystallization was by slow evaporation of its methanol solution yielded light-brown crystals of (I). Yield 0.43 g, 78%: M.pt.: 477–479 K. Anal. Calc. for C₁₆H₂₂ClN₃O₃SSn: C, 39.17; H, 4.52; N, 8.56%. Found: C, 39.16; H, 4.50; N, 8.54%

Structure description top

For background to the biological activity of tin/organotin compounds, see: Gielen & Tiekink (2005). For related studies on organotin compounds, see: Affan et al. (2009); Zukerman-Schpector et al. (2009); Affan et al. (2010).

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular chains along c in the structure of (I). The O–H···O hydrogen bonds are shown as orange dashed lines.
	Fig. 3. Unit-cell contents shown in projection down the c axis in (I). The N–H···Cl hydrogen bonds between layers are shown as brown dashed lines.

Aquachlorido{2-[2-(cyclohexylcarbamothioyl-κS)hydrazinylidene- κN¹]propanoato(2-)}phenyltin(IV) top

Crystal data top

[Sn(C₆H₅)(C₁₀H₁₅N₃O₂S)Cl(H₂O)]	F(000) = 1968
M_r = 490.57	D_x = 1.665 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8808 reflections
a = 16.3904 (9) Å	θ = 2.6–28.3°
b = 19.2018 (10) Å	µ = 1.57 mm⁻¹
c = 13.1127 (7) Å	T = 100 K
β = 108.4421 (7)°	Block, light-brown
V = 3915.0 (4) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	4498 independent reflections
Radiation source: fine-focus sealed tube	3853 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scan	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.613, T_max = 0.746	k = −24→24
18020 measured reflections	l = −16→17

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ²(F_o²) + (0.05P)² + 0.5P] where P = (F_o² + 2F_c²)/3
4498 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.54 e Å⁻³
3 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Sn(C₆H₅)(C₁₀H₁₅N₃O₂S)Cl(H₂O)]	V = 3915.0 (4) Å³
M_r = 490.57	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.3904 (9) Å	µ = 1.57 mm⁻¹
b = 19.2018 (10) Å	T = 100 K
c = 13.1127 (7) Å	0.30 × 0.25 × 0.20 mm
β = 108.4421 (7)°

Data collection top

Bruker SMART APEX diffractometer	4498 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3853 reflections with I > 2σ(I)
T_min = 0.613, T_max = 0.746	R_int = 0.034
18020 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	3 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.54 e Å⁻³
4498 reflections	Δρ_min = −0.53 e Å⁻³
239 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Sn	0.404486 (12)	0.620716 (10)	0.467538 (16)	0.01146 (8)
Cl1	0.34899 (5)	0.69580 (4)	0.30936 (6)	0.01767 (16)
S1	0.32710 (5)	0.68215 (4)	0.57359 (6)	0.01380 (16)
O1	0.41904 (13)	0.54024 (11)	0.36085 (18)	0.0163 (5)
O2	0.34146 (15)	0.47501 (12)	0.22370 (19)	0.0209 (5)
O1W	0.43443 (15)	0.53800 (13)	0.5926 (2)	0.0201 (5)
H1W	0.475 (3)	0.512 (3)	0.590 (5)	0.09 (2)*
H2W	0.406 (3)	0.531 (3)	0.634 (3)	0.066 (17)*
N1	0.16705 (17)	0.65474 (14)	0.5583 (2)	0.0158 (5)
H1N	0.176 (2)	0.6892 (13)	0.602 (2)	0.019 (10)*
N2	0.21381 (16)	0.58361 (13)	0.4501 (2)	0.0151 (5)
N3	0.27999 (16)	0.56696 (13)	0.4134 (2)	0.0140 (5)
C1	0.0801 (2)	0.62496 (16)	0.5200 (3)	0.0182 (7)
H1A	0.0852	0.5735	0.5119	0.022*
C2	0.0277 (2)	0.6546 (2)	0.4129 (3)	0.0275 (8)
H2A	0.0576	0.6459	0.3593	0.033*
H2B	0.0219	0.7056	0.4195	0.033*
C3	−0.0616 (3)	0.6211 (3)	0.3750 (4)	0.0455 (12)
H3A	−0.0958	0.6422	0.3058	0.055*
H3B	−0.0558	0.5707	0.3630	0.055*
C4	−0.1082 (2)	0.6313 (2)	0.4576 (4)	0.0354 (10)
H4A	−0.1207	0.6815	0.4625	0.042*
H4B	−0.1637	0.6061	0.4339	0.042*
C5	−0.0553 (2)	0.6053 (2)	0.5669 (4)	0.0324 (9)
H5A	−0.0496	0.5540	0.5644	0.039*
H5B	−0.0852	0.6163	0.6197	0.039*
C6	0.0344 (2)	0.63821 (19)	0.6035 (3)	0.0230 (7)
H6A	0.0294	0.6890	0.6133	0.028*
H6B	0.0687	0.6181	0.6735	0.028*
C7	0.2306 (2)	0.63535 (16)	0.5207 (3)	0.0140 (6)
C8	0.27078 (19)	0.52131 (16)	0.3388 (2)	0.0147 (6)
C9	0.1909 (2)	0.48168 (17)	0.2862 (3)	0.0204 (7)
H9A	0.1428	0.5030	0.3041	0.031*
H9B	0.1982	0.4334	0.3116	0.031*
H9C	0.1789	0.4825	0.2081	0.031*
C10	0.34849 (19)	0.51063 (16)	0.3033 (3)	0.0155 (6)
C11	0.53637 (18)	0.64917 (15)	0.5141 (2)	0.0131 (6)
C12	0.5831 (2)	0.66164 (17)	0.6212 (3)	0.0198 (7)
H12A	0.5558	0.6584	0.6750	0.024*
C13	0.6698 (2)	0.67889 (19)	0.6493 (3)	0.0226 (7)
H13	0.7013	0.6884	0.7222	0.027*
C14	0.7103 (2)	0.68218 (19)	0.5720 (3)	0.0230 (7)
H14	0.7697	0.6935	0.5919	0.028*
C15	0.6644 (2)	0.66898 (18)	0.4644 (3)	0.0221 (7)
H15	0.6923	0.6708	0.4112	0.027*
C16	0.5775 (2)	0.65323 (17)	0.4362 (3)	0.0187 (7)
H16	0.5457	0.6451	0.3629	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.01020 (12)	0.01204 (12)	0.01312 (13)	0.00088 (7)	0.00509 (8)	−0.00039 (7)
Cl1	0.0226 (4)	0.0173 (4)	0.0131 (4)	0.0036 (3)	0.0056 (3)	0.0019 (3)
S1	0.0125 (3)	0.0155 (4)	0.0143 (4)	0.0011 (3)	0.0054 (3)	−0.0021 (3)
O1	0.0140 (10)	0.0154 (11)	0.0216 (12)	−0.0001 (8)	0.0087 (9)	−0.0032 (9)
O2	0.0226 (12)	0.0207 (12)	0.0239 (13)	−0.0031 (9)	0.0137 (10)	−0.0074 (10)
O1W	0.0162 (11)	0.0218 (12)	0.0270 (13)	0.0088 (9)	0.0137 (10)	0.0105 (10)
N1	0.0133 (12)	0.0166 (14)	0.0200 (14)	0.0002 (10)	0.0089 (11)	−0.0040 (11)
N2	0.0128 (12)	0.0174 (13)	0.0187 (14)	0.0013 (10)	0.0099 (10)	−0.0015 (11)
N3	0.0147 (12)	0.0135 (12)	0.0163 (13)	0.0017 (10)	0.0083 (10)	0.0009 (10)
C1	0.0138 (15)	0.0158 (16)	0.0284 (19)	−0.0014 (11)	0.0117 (14)	−0.0014 (13)
C2	0.0185 (17)	0.045 (2)	0.0203 (18)	−0.0013 (15)	0.0084 (14)	−0.0053 (16)
C3	0.021 (2)	0.078 (4)	0.035 (3)	−0.0079 (19)	0.0054 (17)	−0.024 (2)
C4	0.0161 (17)	0.045 (3)	0.048 (3)	−0.0062 (16)	0.0146 (17)	−0.0146 (19)
C5	0.0234 (19)	0.0272 (19)	0.056 (3)	−0.0001 (15)	0.0258 (19)	0.0030 (18)
C6	0.0174 (16)	0.0292 (18)	0.0270 (19)	0.0058 (14)	0.0136 (14)	0.0069 (15)
C7	0.0163 (15)	0.0127 (14)	0.0148 (15)	0.0012 (11)	0.0073 (12)	0.0023 (12)
C8	0.0147 (14)	0.0155 (15)	0.0151 (15)	0.0018 (11)	0.0066 (12)	−0.0004 (12)
C9	0.0184 (16)	0.0188 (17)	0.0260 (18)	−0.0035 (13)	0.0100 (14)	−0.0066 (14)
C10	0.0165 (15)	0.0137 (15)	0.0184 (16)	0.0006 (12)	0.0085 (12)	0.0009 (12)
C11	0.0113 (13)	0.0123 (14)	0.0164 (15)	0.0010 (11)	0.0056 (11)	0.0023 (12)
C12	0.0166 (15)	0.0265 (18)	0.0186 (17)	−0.0005 (13)	0.0090 (13)	0.0020 (14)
C13	0.0179 (16)	0.034 (2)	0.0126 (16)	−0.0060 (14)	−0.0001 (13)	0.0006 (14)
C14	0.0123 (15)	0.0324 (19)	0.0227 (18)	−0.0044 (13)	0.0034 (13)	0.0030 (15)
C15	0.0147 (15)	0.0342 (19)	0.0198 (17)	−0.0017 (14)	0.0088 (13)	0.0030 (15)
C16	0.0162 (15)	0.0255 (18)	0.0138 (16)	0.0002 (13)	0.0042 (12)	−0.0013 (13)

Geometric parameters (Å, º) top

Sn—C11	2.123 (3)	C3—H3B	0.9900
Sn—O1	2.148 (2)	C4—C5	1.506 (6)
Sn—N3	2.195 (3)	C4—H4A	0.9900
Sn—O1w	2.224 (2)	C4—H4B	0.9900
Sn—Cl1	2.4524 (8)	C5—C6	1.532 (5)
Sn—S1	2.4598 (7)	C5—H5A	0.9900
S1—C7	1.759 (3)	C5—H5B	0.9900
O1—C10	1.295 (4)	C6—H6A	0.9900
O2—C10	1.223 (4)	C6—H6B	0.9900
O1W—H1W	0.84 (5)	C8—C9	1.482 (4)
O1W—H2W	0.83 (5)	C8—C10	1.502 (4)
N1—C7	1.339 (4)	C9—H9A	0.9800
N1—C1	1.469 (4)	C9—H9B	0.9800
N1—H1N	0.86 (3)	C9—H9C	0.9800
N2—C7	1.326 (4)	C11—C12	1.391 (4)
N2—N3	1.357 (3)	C11—C16	1.392 (4)
N3—C8	1.286 (4)	C12—C13	1.390 (4)
C1—C2	1.507 (5)	C12—H12A	0.9500
C1—C6	1.530 (4)	C13—C14	1.377 (5)
C1—H1A	1.0000	C13—H13	0.9500
C2—C3	1.531 (5)	C14—C15	1.395 (5)
C2—H2A	0.9900	C14—H14	0.9500
C2—H2B	0.9900	C15—C16	1.387 (4)
C3—C4	1.524 (6)	C15—H15	0.9500
C3—H3A	0.9900	C16—H16	0.9500

C11—Sn—O1	93.42 (10)	C5—C4—H4B	109.3
C11—Sn—N3	166.35 (10)	C3—C4—H4B	109.3
O1—Sn—N3	74.60 (9)	H4A—C4—H4B	108.0
C11—Sn—O1W	90.27 (10)	C4—C5—C6	111.6 (3)
O1—Sn—O1W	85.55 (9)	C4—C5—H5A	109.3
N3—Sn—O1W	82.43 (9)	C6—C5—H5A	109.3
C11—Sn—Cl1	99.40 (8)	C4—C5—H5B	109.3
O1—Sn—Cl1	87.71 (6)	C6—C5—H5B	109.3
N3—Sn—Cl1	86.84 (7)	H5A—C5—H5B	108.0
O1W—Sn—Cl1	168.53 (7)	C1—C6—C5	110.2 (3)
C11—Sn—S1	111.98 (8)	C1—C6—H6A	109.6
O1—Sn—S1	153.73 (6)	C5—C6—H6A	109.6
N3—Sn—S1	79.37 (7)	C1—C6—H6B	109.6
O1W—Sn—S1	87.63 (6)	C5—C6—H6B	109.6
Cl1—Sn—S1	94.39 (3)	H6A—C6—H6B	108.1
C7—S1—Sn	95.30 (10)	N2—C7—N1	116.8 (3)
C10—O1—Sn	115.62 (18)	N2—C7—S1	128.3 (2)
Sn—O1W—H1W	113 (4)	N1—C7—S1	114.8 (2)
Sn—O1W—H2W	124 (4)	N3—C8—C9	125.3 (3)
H1W—O1W—H2W	123 (5)	N3—C8—C10	114.9 (3)
C7—N1—C1	123.4 (3)	C9—C8—C10	119.8 (3)
C7—N1—H1N	119 (3)	C8—C9—H9A	109.5
C1—N1—H1N	118 (2)	C8—C9—H9B	109.5
C7—N2—N3	114.3 (2)	H9A—C9—H9B	109.5
C8—N3—N2	121.0 (3)	C8—C9—H9C	109.5
C8—N3—Sn	116.1 (2)	H9A—C9—H9C	109.5
N2—N3—Sn	122.70 (19)	H9B—C9—H9C	109.5
N1—C1—C2	112.1 (3)	O2—C10—O1	124.6 (3)
N1—C1—C6	109.4 (3)	O2—C10—C8	118.7 (3)
C2—C1—C6	109.9 (3)	O1—C10—C8	116.6 (3)
N1—C1—H1A	108.4	C12—C11—C16	119.4 (3)
C2—C1—H1A	108.4	C12—C11—Sn	121.3 (2)
C6—C1—H1A	108.4	C16—C11—Sn	119.2 (2)
C1—C2—C3	110.4 (3)	C13—C12—C11	119.9 (3)
C1—C2—H2A	109.6	C13—C12—H12A	120.0
C3—C2—H2A	109.6	C11—C12—H12A	120.0
C1—C2—H2B	109.6	C14—C13—C12	120.4 (3)
C3—C2—H2B	109.6	C14—C13—H13	119.8
H2A—C2—H2B	108.1	C12—C13—H13	119.8
C4—C3—C2	111.0 (3)	C13—C14—C15	120.3 (3)
C4—C3—H3A	109.4	C13—C14—H14	119.9
C2—C3—H3A	109.4	C15—C14—H14	119.9
C4—C3—H3B	109.4	C16—C15—C14	119.3 (3)
C2—C3—H3B	109.4	C16—C15—H15	120.3
H3A—C3—H3B	108.0	C14—C15—H15	120.3
C5—C4—C3	111.5 (3)	C15—C16—C11	120.7 (3)
C5—C4—H4A	109.3	C15—C16—H16	119.7
C3—C4—H4A	109.3	C11—C16—H16	119.7

C11—Sn—S1—C7	−173.02 (13)	N3—N2—C7—S1	−1.7 (4)
O1—Sn—S1—C7	−8.72 (18)	C1—N1—C7—N2	−4.2 (5)
N3—Sn—S1—C7	−0.95 (12)	C1—N1—C7—S1	176.4 (2)
O1W—Sn—S1—C7	−83.69 (12)	Sn—S1—C7—N2	1.9 (3)
Cl1—Sn—S1—C7	85.00 (10)	Sn—S1—C7—N1	−178.8 (2)
C11—Sn—O1—C10	−173.8 (2)	N2—N3—C8—C9	−0.9 (5)
N3—Sn—O1—C10	12.9 (2)	Sn—N3—C8—C9	−176.5 (2)
O1W—Sn—O1—C10	96.2 (2)	N2—N3—C8—C10	177.5 (3)
Cl1—Sn—O1—C10	−74.5 (2)	Sn—N3—C8—C10	1.9 (3)
S1—Sn—O1—C10	20.8 (3)	Sn—O1—C10—O2	164.0 (3)
C7—N2—N3—C8	−174.9 (3)	Sn—O1—C10—C8	−16.3 (3)
C7—N2—N3—Sn	0.4 (4)	N3—C8—C10—O2	−170.7 (3)
C11—Sn—N3—C8	−36.8 (6)	C9—C8—C10—O2	7.9 (5)
O1—Sn—N3—C8	−7.6 (2)	N3—C8—C10—O1	9.6 (4)
O1W—Sn—N3—C8	−95.0 (2)	C9—C8—C10—O1	−171.9 (3)
Cl1—Sn—N3—C8	80.9 (2)	O1—Sn—C11—C12	−135.8 (3)
S1—Sn—N3—C8	176.0 (2)	N3—Sn—C11—C12	−107.6 (5)
C11—Sn—N3—N2	147.7 (4)	O1W—Sn—C11—C12	−50.2 (3)
O1—Sn—N3—N2	176.9 (2)	Cl1—Sn—C11—C12	136.0 (2)
O1W—Sn—N3—N2	89.5 (2)	S1—Sn—C11—C12	37.3 (3)
Cl1—Sn—N3—N2	−94.6 (2)	O1—Sn—C11—C16	42.1 (3)
S1—Sn—N3—N2	0.5 (2)	N3—Sn—C11—C16	70.3 (5)
C7—N1—C1—C2	−77.7 (4)	O1W—Sn—C11—C16	127.7 (3)
C7—N1—C1—C6	160.1 (3)	Cl1—Sn—C11—C16	−46.1 (3)
N1—C1—C2—C3	178.8 (3)	S1—Sn—C11—C16	−144.8 (2)
C6—C1—C2—C3	−59.3 (4)	C16—C11—C12—C13	0.9 (5)
C1—C2—C3—C4	57.3 (5)	Sn—C11—C12—C13	178.8 (3)
C2—C3—C4—C5	−54.5 (5)	C11—C12—C13—C14	−1.5 (5)
C3—C4—C5—C6	54.2 (5)	C12—C13—C14—C15	0.7 (6)
N1—C1—C6—C5	−178.0 (3)	C13—C14—C15—C16	0.7 (5)
C2—C1—C6—C5	58.5 (4)	C14—C15—C16—C11	−1.3 (5)
C4—C5—C6—C1	−56.1 (4)	C12—C11—C16—C15	0.5 (5)
N3—N2—C7—N1	178.9 (3)	Sn—C11—C16—C15	−177.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O1ⁱ	0.84 (5)	1.94 (3)	2.733 (3)	159 (6)
O1w—H2w···O2ⁱⁱ	0.83 (5)	1.81 (2)	2.645 (3)	174 (5)
N1—H1n···Cl1ⁱⁱⁱ	0.86 (3)	2.59 (2)	3.407 (3)	161 (3)

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

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)(C₁₀H₁₅N₃O₂S)Cl(H₂O)]
M_r	490.57
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	16.3904 (9), 19.2018 (10), 13.1127 (7)
β (°)	108.4421 (7)
V (Å³)	3915.0 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
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	0.613, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	18020, 4498, 3853
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.091, 1.19
No. of reflections	4498
No. of parameters	239
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.53

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn—C11	2.123 (3)	Sn—O1w	2.224 (2)
Sn—O1	2.148 (2)	Sn—Cl1	2.4524 (8)
Sn—N3	2.195 (3)	Sn—S1	2.4598 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O1ⁱ	0.84 (5)	1.94 (3)	2.733 (3)	159 (6)
O1w—H2w···O2ⁱⁱ	0.83 (5)	1.81 (2)	2.645 (3)	174 (5)
N1—H1n···Cl1ⁱⁱⁱ	0.86 (3)	2.587 (16)	3.407 (3)	161 (3)

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

Footnotes

‡Additional correspondence author, e-mail: maaffan@frst.unimas.my.

Acknowledgements

This work was financially supported by the Ministry of Science Technology and Innovation (MOSTI) under a research grant (No. 06–01-09-SF0046). The authors would like to thank Universiti Malaysia Sarawak (UNIMAS) for the facilities to carry out the research work and the University of Malaya for support of the crystallographic facility.

References

Affan, M. A., Sam, N. B., Ahmad, F. B. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m924. Web of Science CSD CrossRef IUCr Journals Google Scholar
Affan, M. A., Wan Foo, S., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031–5037. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gielen, M. & Tiekink, E. R. T. (2005). Editors. Metallotherapeutic Drugs and Metal- Based Diagnostic Agents: The Use of Metals in Medicine, pp. 421–439. Chichester: John Wiley & Sons. 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
Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951. Web of Science CrossRef IUCr Journals Google Scholar

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