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

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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.027
• wR factor = 0.091
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.47 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Uiso(max)/Uso(min) ...       4.74 Rati
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8
PLAT736_ALERT_1_C H...A   Calc     1.82(5), Rep     1.81(2) ......       2.50 su-Ra
              H2W  -O2      1.555   6.566

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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%

S3. Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.2 to 1.5U_eq(C). The O– and N-bound H-atoms were located in a difference Fourier map, and was refined with distance restraints of O–H = 0.84 ±0.01 Å and N–H = 0.86±0.01 Å; the U_iso values were freely refined

Computing details

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

	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)

Crystal data

[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) Å^3	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer	4498 independent reflections
Radiation source: fine-focus sealed tube	3853 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
4498 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.54 e Å^−3
3 restraints	Δρmin = −0.53 e Å^−3

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O1^i	0.84 (5)	1.94 (3)	2.733 (3)	159 (6)
O1w—H2w···O2^ii	0.83 (5)	1.81 (2)	2.645 (3)	174 (5)
N1—H1n···Cl1^iii	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.