Aqua-chlorido{2-[2-(cyclo-hexyl-carbamo-thioyl-κS)hydrazinyl-idene-κN]propano-ato(2-)}phenyl-tin(IV).

In the title organotin compound, [Sn(C(6)H(5))(C(10)H(15)N(3)O(2)S)Cl(H(2)O)], 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 mol-ecule in a distorted octa-hedral coordination environment. Coordin-ated water mol-ecules link the organotin mol-ecules by forming O-H⋯O hydrogen bonds with both carbonyl and carboxyl-ate O atoms, leading to 12-membered {⋯OCO⋯HOH⋯}(2) synthons. This results in the formation of supra-molecular 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 = 490.57

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.091

S = 1.19

4498 reflections

239 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.53 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031715/lh5114Isup2.hkl

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

[Sn(C6H5)(C10H15N3O2S)Cl(H2O)]	F(000) = 1968
Mr = 490.57	Dx = 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

Bruker SMART APEX diffractometer	4498 independent reflections
Radiation source: fine-focus sealed tube	3853 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scan	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.613, Tmax = 0.746	k = −24→24
18020 measured reflections	l = −16→17

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(Fo2) + (0.05P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
4498 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.54 e Å−3
3 restraints	Δρmin = −0.53 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) ; (iii) .