Cyclo-pentyl-diphen-yl(4-thio-semi-carbazonopenta-noato-κO)tin(IV).

The Sn atom in the title compound, [Sn(C(5)H(9))(C(6)H(5))(2)(C(6)H(10)N(3)O(2)S)], exists within a tetra-hedral geometry. The -NH(2) group forms a weak hydrogen bond across a center of inversion to the S atom of an adjacent mol-ecule, as well as another weaker hydrogen (across another center of inversion) to the Sn-bound O atom of another mol-ecule. The hydrogen-bonded layer structure is consolidated by a strong hydrogen bond between the -NH- group and the uncoordinated O atom of a third mol-ecule.

Related literature

For the antibacterial and antifungal applications of cyclo­pentyl­diphenyl­tin carboxyl­ates, see: Koshy et al. (2001 ▶). For the crystal structures of cyclo­pentyl­diphenyl­tin derivatives, see: Lo & Ng (2004 ▶); Lo et al. (1999 ▶); Teo et al. (2004 ▶). For the synthesis of levulinic acid thio­semicarbazone, see: Ng (1992 ▶). For a review of the structural chemistry of organotin carboxyl­ates, see: Tiekink (1991 ▶, 1994 ▶).

Experimental

Crystal data

[Sn(C5H9)(C6H5)2(C6H10N3O2S)]

M = 530.24

Triclinic,

a = 9.5780 (1) Å

b = 10.2375 (1) Å

c = 13.4205 (1) Å

α = 86.901 (1)°

β = 83.370 (1)°

γ = 63.667 (1)°

V = 1171.50 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.20 mm−1

T = 100 (2) K

0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.779, T max = 0.889

15020 measured reflections

5350 independent reflections

5186 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.078

S = 1.03

5350 reflections

272 parameters

H-atom parameters constrained

Δρmax = 1.99 e Å−3

Δρmin = −0.91 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011112/tk2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011112/tk2255Isup2.hkl

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

[Sn(C5H9)(C6H5)2(C6H10N3O2S)]	Z = 2
Mr = 530.24	F000 = 540
Triclinic, P1	Dx = 1.503 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.5780 (1) Å	Cell parameters from 9905 reflections
b = 10.2375 (1) Å	θ = 2.4–28.3º
c = 13.4205 (1) Å	µ = 1.20 mm−1
α = 86.901 (1)º	T = 100 (2) K
β = 83.370 (1)º	Irregular block, colorless
γ = 63.667 (1)º	0.30 × 0.15 × 0.10 mm
V = 1171.50 (2) Å3

Bruker SMART APEXII diffractometer	5350 independent reflections
Radiation source: fine-focus sealed tube	5186 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.014
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→12
Tmin = 0.779, Tmax = 0.889	k = −13→13
15020 measured reflections	l = −17→17

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0431P)2 + 2.3757P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
5350 reflections	Δρmax = 1.99 e Å−3
272 parameters	Δρmin = −0.91 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
Sn1	0.400900 (17)	0.628156 (16)	0.232609 (11)	0.01648 (6)
S1	0.24404 (7)	0.05406 (6)	0.56139 (5)	0.02291 (13)
O1	0.4075 (2)	0.63541 (19)	0.38521 (13)	0.0191 (3)
O2	0.1648 (2)	0.66366 (19)	0.38475 (13)	0.0188 (3)
N1	0.1747 (2)	0.4584 (2)	0.57946 (15)	0.0161 (4)
N2	0.1483 (2)	0.3354 (2)	0.58783 (15)	0.0160 (4)
H2N	0.0552	0.3410	0.6087	0.019*
N3	0.4100 (2)	0.2066 (2)	0.54086 (17)	0.0215 (4)
H3N1	0.4187	0.2883	0.5433	0.026*
H3N2	0.4933	0.1248	0.5240	0.026*
C1	0.2123 (3)	0.8151 (3)	0.1783 (2)	0.0269 (5)
H1	0.1189	0.7944	0.1863	0.032*
C2	0.2415 (5)	0.8439 (5)	0.0673 (3)	0.0712 (16)
H2A	0.1932	0.8001	0.0267	0.085*
H2B	0.3553	0.8010	0.0460	0.085*
C3	0.1675 (4)	1.0097 (4)	0.0531 (2)	0.0359 (7)
H3A	0.2491	1.0442	0.0376	0.043*
H3B	0.0987	1.0397	−0.0019	0.043*
C4	0.0732 (5)	1.0696 (4)	0.1530 (3)	0.0495 (9)
H4A	−0.0343	1.0788	0.1542	0.059*
H4B	0.0672	1.1663	0.1663	0.059*
C5	0.1651 (4)	0.9556 (3)	0.2307 (3)	0.0398 (7)
H5A	0.2577	0.9674	0.2456	0.048*
H5B	0.0978	0.9625	0.2940	0.048*
C6	0.4168 (3)	0.4221 (3)	0.19650 (18)	0.0199 (5)
C7	0.4926 (3)	0.2975 (3)	0.2541 (2)	0.0245 (5)
H7	0.5361	0.3044	0.3126	0.029*
C8	0.5049 (3)	0.1635 (3)	0.2263 (2)	0.0285 (6)
H8	0.5560	0.0794	0.2661	0.034*
C9	0.4429 (3)	0.1523 (3)	0.1411 (2)	0.0271 (5)
H9	0.4516	0.0607	0.1223	0.032*
C10	0.3684 (3)	0.2743 (3)	0.08321 (19)	0.0238 (5)
H10	0.3244	0.2668	0.0251	0.029*
C11	0.3575 (3)	0.4079 (3)	0.10956 (19)	0.0225 (5)
H11	0.3093	0.4906	0.0680	0.027*
C12	0.6217 (3)	0.6303 (3)	0.19063 (17)	0.0176 (4)
C13	0.7494 (3)	0.5069 (3)	0.14887 (18)	0.0201 (5)
H13	0.7382	0.4206	0.1403	0.024*
C14	0.8925 (3)	0.5089 (3)	0.11974 (19)	0.0236 (5)
H14	0.9784	0.4245	0.0913	0.028*
C15	0.9095 (3)	0.6343 (3)	0.13229 (19)	0.0243 (5)
H15	1.0070	0.6359	0.1118	0.029*
C16	0.7847 (3)	0.7577 (3)	0.17470 (19)	0.0231 (5)
H16	0.7970	0.8432	0.1841	0.028*
C17	0.6419 (3)	0.7553 (3)	0.20323 (18)	0.0198 (5)
H17	0.5565	0.8400	0.2318	0.024*
C18	0.2692 (3)	0.6595 (2)	0.43182 (18)	0.0163 (4)
C19	0.2537 (3)	0.6844 (3)	0.54288 (18)	0.0184 (4)
H19A	0.2739	0.7692	0.5536	0.022*
H19B	0.3354	0.5982	0.5733	0.022*
C20	0.0950 (3)	0.7117 (3)	0.59732 (18)	0.0194 (5)
H20A	0.0866	0.7515	0.6645	0.023*
H20B	0.0126	0.7872	0.5600	0.023*
C21	0.0628 (3)	0.5805 (2)	0.61014 (17)	0.0162 (4)
C22	−0.0961 (3)	0.6051 (3)	0.65817 (19)	0.0211 (5)
H22A	−0.1493	0.7023	0.6884	0.032*
H22B	−0.0851	0.5313	0.7103	0.032*
H22C	−0.1579	0.5979	0.6073	0.032*
C23	0.2715 (3)	0.2065 (2)	0.56254 (17)	0.0170 (4)

	U11	U22	U33	U12	U13	U23
Sn1	0.01453 (9)	0.01349 (9)	0.02213 (10)	−0.00650 (6)	−0.00357 (6)	0.00085 (6)
S1	0.0168 (3)	0.0119 (3)	0.0404 (4)	−0.0064 (2)	−0.0043 (2)	0.0007 (2)
O1	0.0150 (8)	0.0209 (8)	0.0235 (8)	−0.0098 (7)	−0.0020 (6)	−0.0008 (6)
O2	0.0167 (8)	0.0197 (8)	0.0223 (8)	−0.0099 (7)	−0.0036 (6)	0.0004 (6)
N1	0.0180 (9)	0.0135 (9)	0.0185 (9)	−0.0081 (8)	−0.0033 (7)	−0.0001 (7)
N2	0.0139 (9)	0.0128 (9)	0.0219 (9)	−0.0065 (7)	−0.0021 (7)	0.0007 (7)
N3	0.0148 (9)	0.0140 (9)	0.0349 (11)	−0.0058 (8)	0.0000 (8)	−0.0047 (8)
C1	0.0213 (12)	0.0260 (13)	0.0251 (12)	−0.0028 (10)	−0.0042 (10)	0.0019 (10)
C2	0.046 (2)	0.068 (3)	0.040 (2)	0.023 (2)	0.0084 (16)	0.0231 (19)
C3	0.0378 (16)	0.0442 (18)	0.0334 (15)	−0.0241 (14)	−0.0144 (12)	0.0166 (13)
C4	0.049 (2)	0.0292 (16)	0.064 (2)	−0.0123 (15)	−0.0080 (18)	0.0046 (15)
C5	0.0435 (18)	0.0289 (15)	0.0423 (17)	−0.0111 (14)	−0.0067 (14)	0.0004 (13)
C6	0.0214 (11)	0.0190 (11)	0.0228 (11)	−0.0120 (10)	−0.0032 (9)	0.0000 (9)
C7	0.0274 (13)	0.0209 (12)	0.0287 (13)	−0.0120 (10)	−0.0120 (10)	0.0026 (10)
C8	0.0327 (14)	0.0183 (12)	0.0366 (14)	−0.0120 (11)	−0.0105 (11)	0.0048 (10)
C9	0.0285 (14)	0.0221 (12)	0.0323 (14)	−0.0124 (11)	−0.0035 (11)	−0.0021 (10)
C10	0.0257 (13)	0.0257 (13)	0.0224 (12)	−0.0133 (11)	−0.0020 (10)	−0.0032 (9)
C11	0.0236 (12)	0.0205 (12)	0.0230 (12)	−0.0091 (10)	−0.0052 (9)	0.0021 (9)
C12	0.0163 (11)	0.0177 (11)	0.0186 (10)	−0.0072 (9)	−0.0035 (8)	0.0027 (8)
C13	0.0215 (12)	0.0169 (11)	0.0209 (11)	−0.0075 (9)	−0.0030 (9)	0.0021 (9)
C14	0.0188 (12)	0.0238 (12)	0.0227 (12)	−0.0050 (10)	−0.0008 (9)	0.0009 (9)
C15	0.0200 (12)	0.0322 (14)	0.0232 (12)	−0.0144 (11)	−0.0020 (9)	0.0040 (10)
C16	0.0265 (13)	0.0260 (12)	0.0233 (12)	−0.0171 (11)	−0.0041 (10)	0.0015 (9)
C17	0.0194 (11)	0.0185 (11)	0.0211 (11)	−0.0079 (9)	−0.0026 (9)	−0.0003 (9)
C18	0.0165 (11)	0.0098 (9)	0.0234 (11)	−0.0063 (8)	−0.0023 (8)	−0.0002 (8)
C19	0.0206 (11)	0.0142 (10)	0.0228 (11)	−0.0095 (9)	−0.0038 (9)	−0.0014 (8)
C20	0.0202 (11)	0.0143 (10)	0.0226 (11)	−0.0064 (9)	−0.0013 (9)	−0.0029 (8)
C21	0.0163 (11)	0.0157 (10)	0.0162 (10)	−0.0063 (9)	−0.0033 (8)	−0.0009 (8)
C22	0.0172 (11)	0.0209 (11)	0.0234 (11)	−0.0070 (9)	−0.0006 (9)	−0.0032 (9)
C23	0.0173 (11)	0.0139 (10)	0.0203 (11)	−0.0068 (9)	−0.0050 (8)	0.0006 (8)

Sn1—O1	2.063 (2)	C7—H7	0.9500
Sn1—C1	2.131 (3)	C8—C9	1.379 (4)
Sn1—C6	2.125 (2)	C8—H8	0.9500
Sn1—C12	2.134 (2)	C9—C10	1.380 (4)
S1—C23	1.695 (2)	C9—H9	0.9500
O1—C18	1.320 (3)	C10—C11	1.387 (4)
O2—C18	1.227 (3)	C10—H10	0.9500
N1—C21	1.283 (3)	C11—H11	0.9500
N1—N2	1.387 (3)	C12—C13	1.398 (3)
N2—C23	1.350 (3)	C12—C17	1.399 (3)
N2—H2N	0.8800	C13—C14	1.391 (4)
N3—C23	1.325 (3)	C13—H13	0.9500
N3—H3N1	0.8800	C14—C15	1.384 (4)
N3—H3N2	0.8800	C14—H14	0.9500
C1—C5	1.492 (4)	C15—C16	1.389 (4)
C1—C2	1.522 (4)	C15—H15	0.9500
C1—H1	1.0000	C16—C17	1.388 (4)
C2—C3	1.532 (5)	C16—H16	0.9500
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C18—C19	1.505 (3)
C3—C4	1.519 (5)	C19—C20	1.520 (3)
C3—H3A	0.9900	C19—H19A	0.9900
C3—H3B	0.9900	C19—H19B	0.9900
C4—C5	1.547 (5)	C20—C21	1.503 (3)
C4—H4A	0.9900	C20—H20A	0.9900
C4—H4B	0.9900	C20—H20B	0.9900
C5—H5A	0.9900	C21—C22	1.499 (3)
C5—H5B	0.9900	C22—H22A	0.9800
C6—C11	1.396 (3)	C22—H22B	0.9800
C6—C7	1.398 (3)	C22—H22C	0.9800
C7—C8	1.393 (4)
O1—Sn1—C1	112.7 (1)	C8—C9—H9	120.0
O1—Sn1—C6	108.6 (1)	C10—C9—H9	120.0
O1—Sn1—C12	95.9 (1)	C9—C10—C11	120.2 (2)
C1—Sn1—C6	116.5 (1)	C9—C10—H10	119.9
C1—Sn1—C12	112.1 (1)	C11—C10—H10	119.9
C6—Sn1—C12	109.2 (1)	C10—C11—C6	120.7 (2)
Sn1—O1—C18	109.3 (1)	C10—C11—H11	119.7
C21—N1—N2	118.3 (2)	C6—C11—H11	119.7
C23—N2—N1	117.11 (19)	C13—C12—C17	118.4 (2)
C23—N2—H2N	121.4	C13—C12—Sn1	120.71 (18)
N1—N2—H2N	121.4	C17—C12—Sn1	120.94 (18)
C23—N3—H3N1	120.0	C14—C13—C12	120.8 (2)
C23—N3—H3N2	120.0	C14—C13—H13	119.6
H3N1—N3—H3N2	120.0	C12—C13—H13	119.6
C5—C1—C2	106.2 (3)	C15—C14—C13	119.9 (2)
C5—C1—Sn1	116.7 (2)	C15—C14—H14	120.1
C2—C1—Sn1	113.0 (2)	C13—C14—H14	120.1
C5—C1—H1	106.8	C14—C15—C16	120.4 (2)
C2—C1—H1	106.8	C14—C15—H15	119.8
Sn1—C1—H1	106.8	C16—C15—H15	119.8
C1—C2—C3	106.9 (3)	C17—C16—C15	119.5 (2)
C1—C2—H2A	110.3	C17—C16—H16	120.2
C3—C2—H2A	110.3	C15—C16—H16	120.2
C1—C2—H2B	110.3	C16—C17—C12	121.1 (2)
C3—C2—H2B	110.3	C16—C17—H17	119.5
H2A—C2—H2B	108.6	C12—C17—H17	119.5
C4—C3—C2	104.5 (3)	O2—C18—O1	120.5 (2)
C4—C3—H3A	110.9	O2—C18—C19	125.2 (2)
C2—C3—H3A	110.9	O1—C18—C19	114.2 (2)
C4—C3—H3B	110.9	C18—C19—C20	114.6 (2)
C2—C3—H3B	110.9	C18—C19—H19A	108.6
H3A—C3—H3B	108.9	C20—C19—H19A	108.6
C3—C4—C5	104.1 (3)	C18—C19—H19B	108.6
C3—C4—H4A	110.9	C20—C19—H19B	108.6
C5—C4—H4A	110.9	H19A—C19—H19B	107.6
C3—C4—H4B	110.9	C21—C20—C19	115.40 (19)
C5—C4—H4B	110.9	C21—C20—H20A	108.4
H4A—C4—H4B	109.0	C19—C20—H20A	108.4
C1—C5—C4	102.4 (3)	C21—C20—H20B	108.4
C1—C5—H5A	111.3	C19—C20—H20B	108.4
C4—C5—H5A	111.3	H20A—C20—H20B	107.5
C1—C5—H5B	111.3	N1—C21—C22	126.5 (2)
C4—C5—H5B	111.3	N1—C21—C20	116.6 (2)
H5A—C5—H5B	109.2	C22—C21—C20	116.8 (2)
C11—C6—C7	118.4 (2)	C21—C22—H22A	109.5
C11—C6—Sn1	119.38 (18)	C21—C22—H22B	109.5
C7—C6—Sn1	122.09 (18)	H22A—C22—H22B	109.5
C8—C7—C6	120.4 (2)	C21—C22—H22C	109.5
C8—C7—H7	119.8	H22A—C22—H22C	109.5
C6—C7—H7	119.8	H22B—C22—H22C	109.5
C9—C8—C7	120.2 (3)	N3—C23—N2	117.2 (2)
C9—C8—H8	119.9	N3—C23—S1	123.29 (18)
C7—C8—H8	119.9	N2—C23—S1	119.54 (18)
C8—C9—C10	120.0 (2)
C6—Sn1—O1—C18	−77.70 (16)	C9—C10—C11—C6	−2.2 (4)
C1—Sn1—O1—C18	52.80 (17)	C7—C6—C11—C10	2.5 (4)
C12—Sn1—O1—C18	169.72 (15)	Sn1—C6—C11—C10	179.0 (2)
C21—N1—N2—C23	−174.8 (2)	O1—Sn1—C12—C13	110.54 (19)
O1—Sn1—C1—C5	32.7 (3)	C6—Sn1—C12—C13	−1.5 (2)
C6—Sn1—C1—C5	159.1 (2)	C1—Sn1—C12—C13	−132.09 (19)
C12—Sn1—C1—C5	−74.2 (2)	O1—Sn1—C12—C17	−70.09 (19)
O1—Sn1—C1—C2	156.3 (3)	C6—Sn1—C12—C17	177.87 (18)
C6—Sn1—C1—C2	−77.3 (3)	C1—Sn1—C12—C17	47.3 (2)
C12—Sn1—C1—C2	49.4 (3)	C17—C12—C13—C14	−0.6 (4)
C5—C1—C2—C3	−15.5 (4)	Sn1—C12—C13—C14	178.79 (18)
Sn1—C1—C2—C3	−144.7 (3)	C12—C13—C14—C15	0.2 (4)
C1—C2—C3—C4	−9.9 (5)	C13—C14—C15—C16	0.6 (4)
C2—C3—C4—C5	30.7 (4)	C14—C15—C16—C17	−0.9 (4)
C2—C1—C5—C4	34.0 (4)	C15—C16—C17—C12	0.4 (4)
Sn1—C1—C5—C4	161.0 (2)	C13—C12—C17—C16	0.3 (4)
C3—C4—C5—C1	−40.3 (4)	Sn1—C12—C17—C16	−179.07 (18)
O1—Sn1—C6—C11	155.98 (19)	Sn1—O1—C18—O2	5.1 (3)
C1—Sn1—C6—C11	27.6 (2)	Sn1—O1—C18—C19	−173.25 (14)
C12—Sn1—C6—C11	−100.6 (2)	O2—C18—C19—C20	2.0 (3)
O1—Sn1—C6—C7	−27.7 (2)	O1—C18—C19—C20	−179.78 (19)
C1—Sn1—C6—C7	−156.1 (2)	C18—C19—C20—C21	72.7 (3)
C12—Sn1—C6—C7	75.7 (2)	N2—N1—C21—C22	2.0 (3)
C11—C6—C7—C8	−1.6 (4)	N2—N1—C21—C20	−178.51 (19)
Sn1—C6—C7—C8	−178.0 (2)	C19—C20—C21—N1	3.9 (3)
C6—C7—C8—C9	0.4 (4)	C19—C20—C21—C22	−176.6 (2)
C7—C8—C9—C10	−0.1 (4)	N1—N2—C23—N3	6.1 (3)
C8—C9—C10—C11	1.0 (4)	N1—N2—C23—S1	−174.76 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O2i	0.88	2.12	2.975 (3)	163
N3—H3n1···O1ii	0.88	2.43	3.121 (3)	136
N3—H3n2···S1iii	0.88	2.54	3.389 (2)	161

Sn1—O1	2.063 (2)
Sn1—C1	2.131 (3)
Sn1—C6	2.125 (2)
Sn1—C12	2.134 (2)

O1—Sn1—C1	112.7 (1)
O1—Sn1—C6	108.6 (1)
O1—Sn1—C12	95.9 (1)
C1—Sn1—C6	116.5 (1)
C1—Sn1—C12	112.1 (1)
C6—Sn1—C12	109.2 (1)
Sn1—O1—C18	109.3 (1)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O2i	0.88	2.12	2.975 (3)	163
N3—H3n1⋯O1ii	0.88	2.43	3.121 (3)	136
N3—H3n2⋯S1iii	0.88	2.54	3.389 (2)	161

Symmetry codes: (i) ; (ii) ; (iii) .