Aqua­chloridodimethyl­phenyltin(IV)–15-crown-5 (2/1)

Armaghan, M.; Amini, M.M.; Azadmehr, A.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536808011070

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m721

doi:10.1107/S1600536808011070

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Aquachloridodimethylphenyltin(IV)–15-crown-5 (2/1)

Mahsa Armaghan,^a Mostafa M. Amini,^a Amirreza Azadmehr,^a Shan Gao ^b and Seik Weng Ng ^c ^*

^aDepartment of Chemistry, Shahid Beheshti University, Tehran, Iran, ^bSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 30 January 2008; accepted 20 April 2008; online 26 April 2008)

The Sn^IV atom in the title compound, 2[Sn(CH₃)₂(C₆H₅)Cl(H₂O)]·C₁₀H₂₀O₅, exists in a trans-C₃SnClO trigonal bipyramidal geometry in which the organo substituents occupy the equatorial sites. The coordinated water molecule forms two hydrogen bonds to the 15-crown-5 molecule, which is disordered about a center of inversion.

Related literature

For `outer-sphere coordination' organotin complexes with 15-crown-5, see: Amini et al. (1994 ); Chee et al. (2003 ); Yap et al. (1996 ). For the refinement of 15-crown-5 type crystal structures that are disordered about a center of inversion, see: Ng (2005 ). For the analogous adduct of SnCl(CH₃)₂(C₆H₅)(H₂O) with 18-crown-6, see: Amini et al. (2002 ).

Experimental

Crystal data

2[Sn(CH₃)₂(C₆H₅)Cl(H₂O)]·C₁₀H₂₀O₅
M_r = 778.91
Monoclinic, P 2₁ /n
a = 9.8700 (3) Å
b = 18.9814 (5) Å
c = 9.8770 (3) Å
β = 113.636 (1)°
V = 1695.2 (1) Å³
Z = 2
Mo Kα radiation
μ = 1.67 mm⁻¹
T = 295 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.534, T_max = 0.732
16379 measured reflections
3869 independent reflections
3433 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.128
S = 1.06
3869 reflections
159 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 1.29 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.115 (5)
Sn1—C2	2.122 (5)
Sn1—C3	2.139 (4)
Sn1—O1w	2.472 (3)
Sn1—Cl1	2.485 (1)

C1—Sn1—C2	120.2 (2)
C1—Sn1—C3	121.1 (2)
C2—Sn1—C3	116.0 (2)
O1w—Sn1—Cl1	176.1 (1)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011070/tk2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011070/tk2247Isup2.hkl

checkCIF report

Comment top

Water-coordinated triorganotin salts form "outer-sphere coordination" complexes with crown ethers. In these, the water molecules interact with the crown ether through hydrogen bonds (Amini et al., 1994; Chee et al., 2003; Yap et al., 1996). The refinement of such crystal structures present special difficulties when the odd-numbered crown ether is disordered about a center of inversion. The refinement of such crystal structures has been described in detail (Ng, 2005). The mixed-organo Sn^IV title compound, (I), has the tin atom in a trans-C₃SnClO trigonal bipyramidal geometry, Fig. 1 & Table 1, in which the electronegative substituents occupy the axial sites. The coordinated water molecule forms two hydrogen bonds to the 15-crown-5, which is disordered about a center-of-inversion; Table 2.

Related literature top

For `outer-sphere coordination' organotin complexes with 15-crown-5, see: Amini et al. (1994); Chee et al. (2003); Yap et al. (1996). For the refinement of 15-crown-5 type crystal structures that are disordered about a center of inversion, see: Ng (2005). For the analogous adduct of aqua Sn(CH₃)₂(C₆H₅)Cl with 18-crown-6, see: Amini et al. (2002).

Experimental top

ChlorodimethylphenylSn^IV was synthesized by the cleavage of dimethyldiphenyltin with hydrogen chloride in a methanol/carbon tetrachloride mixture at 283 K and was purified by distillation at 363 K/1 Torr. ChlorodimethylphenylSn^IV (0.26 g, 1 mmol) and 15-crown-5 (0.22 g, 1 mmol) were dissolved in ethanol (20 ml). The co-crystal (I), m.p. 347–349 K, separated when the solvent was allowed to evaporate. ¹H-NMR in CDCl₃: 0.90 (CH₃), 1.60 (H₂O), 3.72 (CH₂), 7.27–7.70 (C₆H₅) p.p.m. ¹¹⁹Sn NMR 115.7 p.p.m. ²J(¹¹⁹Sn–¹H) = 60 Hz.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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).

Figures top

Fig. 1. Molecular structure of (I); ellipsoids are drawn at the 30% probability level, and H atoms as spheres of arbitrary radius. The 15-crown-5 is disordered about a center of inversion, only one orientation is shown for reasons of clarity. Dashed lines denote the water···crown-ether hydrogen bonds. Unlabelled atoms are related by the symmetry operation -x + 2, -y + 1, -z + 2.

Aquachloridodimethylphenyltin(IV)–15-crown-5 (2/1) top

Crystal data top

2[Sn(CH₃)₂(C₆H₅)Cl(H₂O)]·C₁₀H₂₀O₅	F(000) = 784
M_r = 778.91	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13887 reflections
a = 9.8700 (3) Å	θ = 3.1–27.4°
b = 18.9814 (5) Å	µ = 1.67 mm⁻¹
c = 9.8770 (3) Å	T = 295 K
β = 113.636 (1)°	Block, colorless
V = 1695.2 (1) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	3869 independent reflections
Radiation source: fine-focus sealed tube	3433 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.4°, θ_min = 3.1°
ω scans	h = −10→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −24→24
T_min = 0.534, T_max = 0.732	l = −12→12
16379 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0816P)² + 1.7228P] where P = (F_o² + 2F_c²)/3
3869 reflections	(Δ/σ)_max = 0.001
159 parameters	Δρ_max = 1.29 e Å⁻³
30 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

2[Sn(CH₃)₂(C₆H₅)Cl(H₂O)]·C₁₀H₂₀O₅	V = 1695.2 (1) Å³
M_r = 778.91	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8700 (3) Å	µ = 1.67 mm⁻¹
b = 18.9814 (5) Å	T = 295 K
c = 9.8770 (3) Å	0.30 × 0.25 × 0.20 mm
β = 113.636 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3869 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3433 reflections with I > 2σ(I)
T_min = 0.534, T_max = 0.732	R_int = 0.023
16379 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	30 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.06	Δρ_max = 1.29 e Å⁻³
3869 reflections	Δρ_min = −1.14 e Å⁻³
159 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.55993 (3)	0.385283 (13)	0.73184 (3)	0.04272 (13)
Cl1	0.31360 (13)	0.32890 (8)	0.60646 (14)	0.0700 (3)
O1w	0.7986 (3)	0.44517 (17)	0.8682 (4)	0.0634 (8)
H1w	0.7920	0.4866	0.8431	0.095*
H2w	0.8636	0.4260	0.8495	0.095*
C1	0.6070 (6)	0.3380 (3)	0.9397 (6)	0.0719 (14)
H1A	0.6438	0.3730	1.0159	0.108*
H1B	0.6802	0.3019	0.9571	0.108*
H1C	0.5184	0.3175	0.9406	0.108*
C2	0.4774 (6)	0.4899 (3)	0.6902 (7)	0.0696 (13)
H2A	0.5512	0.5202	0.6813	0.104*
H2B	0.4537	0.5056	0.7704	0.104*
H2C	0.3901	0.4910	0.6000	0.104*
C3	0.6535 (4)	0.34520 (18)	0.5860 (4)	0.0448 (8)
C4	0.5616 (6)	0.3317 (2)	0.4393 (5)	0.0584 (10)
H4	0.4599	0.3374	0.4072	0.070*
C5	0.6219 (7)	0.3095 (3)	0.3396 (6)	0.0741 (14)
H5	0.5592	0.2999	0.2422	0.089*
C6	0.7687 (7)	0.3019 (3)	0.3827 (6)	0.0749 (14)
H6	0.8073	0.2881	0.3150	0.090*
C7	0.8608 (6)	0.3144 (3)	0.5261 (7)	0.0719 (13)
H7	0.9623	0.3087	0.5563	0.086*
C8	0.8038 (5)	0.3356 (3)	0.6281 (5)	0.0602 (11)
H8	0.8678	0.3435	0.7259	0.072*
O1	0.8394 (11)	0.5945 (5)	0.8704 (10)	0.0982 (12)	0.50
O2	1.0758 (10)	0.5345 (4)	0.8227 (10)	0.0982 (12)	0.50
O3	1.0975 (10)	0.4055 (5)	0.9549 (9)	0.0982 (12)	0.50
O4	1.1086 (10)	0.4378 (5)	1.2332 (10)	0.0982 (12)	0.50
O5	0.9190 (10)	0.5479 (5)	1.1592 (10)	0.0982 (12)	0.50
C9	0.9218 (17)	0.6312 (6)	0.8003 (17)	0.0922 (11)	0.50
H9A	0.8597	0.6661	0.7317	0.111*	0.50
H9B	1.0062	0.6550	0.8739	0.111*	0.50
C10	0.9708 (14)	0.5796 (6)	0.7224 (12)	0.0922 (11)	0.50
H10A	0.8869	0.5523	0.6574	0.111*	0.50
H10B	1.0140	0.6034	0.6622	0.111*	0.50
C11	1.1043 (16)	0.4717 (5)	0.7580 (12)	0.0922 (11)	0.50
H11A	1.1598	0.4829	0.6990	0.111*	0.50
H11B	1.0118	0.4498	0.6943	0.111*	0.50
C12	1.1889 (15)	0.4240 (7)	0.8775 (15)	0.0922 (11)	0.50
H12A	1.2159	0.3821	0.8379	0.111*	0.50
H12B	1.2788	0.4469	0.9443	0.111*	0.50
C13	1.1716 (15)	0.3633 (6)	1.0805 (11)	0.0922 (11)	0.50
H13A	1.2727	0.3797	1.1304	0.111*	0.50
H13B	1.1744	0.3150	1.0497	0.111*	0.50
C14	1.1003 (19)	0.3657 (6)	1.1805 (15)	0.0922 (11)	0.50
H14A	1.1492	0.3340	1.2629	0.111*	0.50
H14B	0.9978	0.3512	1.1308	0.111*	0.50
C15	1.0198 (14)	0.4487 (6)	1.3105 (12)	0.0922 (11)	0.50
H15A	0.9783	0.4036	1.3200	0.111*	0.50
H15B	1.0831	0.4641	1.4094	0.111*	0.50
C16	0.9041 (13)	0.4965 (6)	1.2534 (15)	0.0922 (11)	0.50
H16A	0.8925	0.5199	1.3353	0.111*	0.50
H16B	0.8138	0.4704	1.1999	0.111*	0.50
C17	0.7917 (15)	0.5900 (8)	1.0850 (13)	0.0922 (11)	0.50
H17A	0.7720	0.6189	1.1561	0.111*	0.50
H17B	0.7066	0.5599	1.0357	0.111*	0.50
C18	0.8149 (16)	0.6343 (6)	0.9783 (12)	0.0922 (11)	0.50
H18A	0.7289	0.6641	0.9308	0.111*	0.50
H18B	0.8995	0.6645	1.0283	0.111*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04543 (19)	0.04251 (18)	0.03998 (18)	−0.00211 (9)	0.01686 (13)	0.00193 (8)
Cl1	0.0538 (6)	0.0880 (8)	0.0622 (7)	−0.0244 (6)	0.0171 (5)	−0.0039 (6)
O1w	0.0542 (16)	0.0637 (18)	0.068 (2)	−0.0146 (14)	0.0198 (14)	−0.0190 (15)
C1	0.072 (3)	0.082 (3)	0.052 (3)	−0.010 (3)	0.015 (2)	0.019 (2)
C2	0.067 (3)	0.053 (2)	0.087 (4)	0.007 (2)	0.029 (3)	0.007 (2)
C3	0.0526 (19)	0.0369 (16)	0.0439 (19)	−0.0036 (15)	0.0183 (16)	0.0006 (14)
C4	0.066 (3)	0.062 (2)	0.041 (2)	0.004 (2)	0.0158 (18)	−0.0013 (17)
C5	0.097 (4)	0.076 (3)	0.049 (3)	0.005 (3)	0.028 (3)	−0.006 (2)
C6	0.110 (4)	0.061 (3)	0.074 (3)	0.003 (3)	0.058 (3)	−0.008 (2)
C7	0.071 (3)	0.071 (3)	0.086 (4)	0.006 (2)	0.044 (3)	−0.006 (3)
C8	0.058 (2)	0.069 (3)	0.055 (2)	−0.006 (2)	0.024 (2)	−0.013 (2)
O1	0.094 (3)	0.106 (3)	0.088 (3)	0.004 (3)	0.031 (2)	0.003 (2)
O2	0.094 (3)	0.106 (3)	0.088 (3)	0.004 (3)	0.031 (2)	0.003 (2)
O3	0.094 (3)	0.106 (3)	0.088 (3)	0.004 (3)	0.031 (2)	0.003 (2)
O4	0.094 (3)	0.106 (3)	0.088 (3)	0.004 (3)	0.031 (2)	0.003 (2)
O5	0.094 (3)	0.106 (3)	0.088 (3)	0.004 (3)	0.031 (2)	0.003 (2)
C9	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C10	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C11	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C12	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C13	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C14	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C15	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C16	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C17	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)
C18	0.092 (2)	0.104 (3)	0.090 (3)	0.007 (2)	0.046 (2)	−0.005 (2)

Geometric parameters (Å, º) top

Sn1—C1	2.115 (5)	O4—C15	1.389 (8)
Sn1—C2	2.122 (5)	O4—C14	1.454 (9)
Sn1—C3	2.139 (4)	O5—C16	1.397 (8)
Sn1—O1w	2.472 (3)	O5—C17	1.420 (9)
Sn1—Cl1	2.485 (1)	C9—C10	1.442 (9)
O1w—H1w	0.8200	C9—H9A	0.9700
O1w—H2w	0.8200	C9—H9B	0.9700
C1—H1A	0.9600	C10—H10A	0.9700
C1—H1B	0.9600	C10—H10B	0.9700
C1—H1C	0.9600	C11—C12	1.455 (9)
C2—H2A	0.9600	C11—H11A	0.9700
C2—H2B	0.9600	C11—H11B	0.9700
C2—H2C	0.9600	C12—H12A	0.9700
C3—C8	1.383 (6)	C12—H12B	0.9700
C3—C4	1.390 (6)	C13—C14	1.425 (8)
C4—C5	1.404 (7)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.345 (8)	C14—H14A	0.9700
C5—H5	0.9300	C14—H14B	0.9700
C6—C7	1.362 (8)	C15—C16	1.388 (8)
C6—H6	0.9300	C15—H15A	0.9700
C7—C8	1.396 (7)	C15—H15B	0.9700
C7—H7	0.9300	C16—H16A	0.9700
C8—H8	0.9300	C16—H16B	0.9700
O1—C18	1.404 (9)	C17—C18	1.437 (8)
O1—C9	1.442 (9)	C17—H17A	0.9700
O2—C10	1.402 (8)	C17—H17B	0.9700
O2—C11	1.433 (9)	C18—H18A	0.9700
O3—C13	1.410 (9)	C18—H18B	0.9700
O3—C12	1.441 (9)

C1—Sn1—C2	120.2 (2)	O2—C10—C9	110.4 (8)
C1—Sn1—C3	121.1 (2)	O2—C10—H10A	109.6
C2—Sn1—C3	116.0 (2)	C9—C10—H10A	109.6
C1—Sn1—O1w	82.9 (2)	O2—C10—H10B	109.6
C2—Sn1—O1w	83.3 (2)	C9—C10—H10B	109.6
C3—Sn1—O1w	87.5 (1)	H10A—C10—H10B	108.1
C1—Sn1—Cl1	95.2 (2)	O2—C11—C12	107.9 (8)
C2—Sn1—Cl1	94.8 (2)	O2—C11—H11A	110.1
C3—Sn1—Cl1	96.4 (1)	C12—C11—H11A	110.1
O1w—Sn1—Cl1	176.1 (1)	O2—C11—H11B	110.1
Sn1—O1w—H1w	109.5	C12—C11—H11B	110.1
Sn1—O1w—H2w	109.5	H11A—C11—H11B	108.4
H1w—O1w—H2w	109.5	O3—C12—C11	107.7 (8)
Sn1—C1—H1A	109.5	O3—C12—H12A	110.2
Sn1—C1—H1B	109.5	C11—C12—H12A	110.2
H1A—C1—H1B	109.5	O3—C12—H12B	110.2
Sn1—C1—H1C	109.5	C11—C12—H12B	110.2
H1A—C1—H1C	109.5	H12A—C12—H12B	108.5
H1B—C1—H1C	109.5	O3—C13—C14	111.5 (8)
Sn1—C2—H2A	109.5	O3—C13—H13A	109.3
Sn1—C2—H2B	109.5	C14—C13—H13A	109.3
H2A—C2—H2B	109.5	O3—C13—H13B	109.3
Sn1—C2—H2C	109.5	C14—C13—H13B	109.3
H2A—C2—H2C	109.5	H13A—C13—H13B	108.0
H2B—C2—H2C	109.5	C13—C14—O4	107.7 (8)
C8—C3—C4	117.5 (4)	C13—C14—H14A	110.2
C8—C3—Sn1	123.0 (3)	O4—C14—H14A	110.2
C4—C3—Sn1	119.3 (3)	C13—C14—H14B	110.2
C3—C4—C5	120.2 (5)	O4—C14—H14B	110.2
C3—C4—H4	119.9	H14A—C14—H14B	108.5
C5—C4—H4	119.9	C16—C15—O4	118.2 (8)
C6—C5—C4	121.1 (5)	C16—C15—H15A	107.8
C6—C5—H5	119.5	O4—C15—H15A	107.8
C4—C5—H5	119.5	C16—C15—H15B	107.8
C5—C6—C7	119.7 (5)	O4—C15—H15B	107.8
C5—C6—H6	120.1	H15A—C15—H15B	107.1
C7—C6—H6	120.1	C15—C16—O5	116.0 (8)
C6—C7—C8	120.4 (5)	C15—C16—H16A	108.3
C6—C7—H7	119.8	O5—C16—H16A	108.3
C8—C7—H7	119.8	C15—C16—H16B	108.3
C3—C8—C7	121.0 (5)	O5—C16—H16B	108.3
C3—C8—H8	119.5	H16A—C16—H16B	107.4
C7—C8—H8	119.5	O5—C17—C18	109.8 (8)
C18—O1—C9	114.0 (8)	O5—C17—H17A	109.7
C10—O2—C11	114.5 (8)	C18—C17—H17A	109.7
C13—O3—C12	113.0 (7)	O5—C17—H17B	109.7
C15—O4—C14	112.3 (8)	C18—C17—H17B	109.7
C16—O5—C17	115.4 (8)	H17A—C17—H17B	108.2
C10—C9—O1	107.7 (8)	O1—C18—C17	111.6 (8)
C10—C9—H9A	110.2	O1—C18—H18A	109.3
O1—C9—H9A	110.2	C17—C18—H18A	109.3
C10—C9—H9B	110.2	O1—C18—H18B	109.3
O1—C9—H9B	110.2	C17—C18—H18B	109.3
H9A—C9—H9B	108.5	H18A—C18—H18B	108.0

C1—Sn1—C3—C8	−54.1 (4)	C18—O1—C9—C10	165.5 (11)
C2—Sn1—C3—C8	107.3 (4)	C11—O2—C10—C9	165.4 (11)
O1w—Sn1—C3—C8	26.0 (4)	O1—C9—C10—O2	−67.6 (15)
Cl1—Sn1—C3—C8	−154.1 (3)	C10—O2—C11—C12	−167.9 (11)
C1—Sn1—C3—C4	129.8 (3)	C13—O3—C12—C11	−175.6 (11)
C2—Sn1—C3—C4	−68.8 (4)	O2—C11—C12—O3	63.6 (15)
O1w—Sn1—C3—C4	−150.1 (3)	C12—O3—C13—C14	160.1 (12)
Cl1—Sn1—C3—C4	29.7 (3)	O3—C13—C14—O4	−63.5 (16)
C8—C3—C4—C5	−0.2 (7)	C15—O4—C14—C13	169.2 (11)
Sn1—C3—C4—C5	176.1 (4)	C14—O4—C15—C16	−117.0 (15)
C3—C4—C5—C6	−1.1 (8)	O4—C15—C16—O5	−24 (2)
C4—C5—C6—C7	1.4 (9)	C17—O5—C16—C15	171.3 (13)
C5—C6—C7—C8	−0.6 (9)	C16—O5—C17—C18	−172.7 (12)
C4—C3—C8—C7	1.1 (7)	C9—O1—C18—C17	−155.4 (12)
Sn1—C3—C8—C7	−175.1 (4)	O5—C17—C18—O1	61.1 (16)
C6—C7—C8—C3	−0.7 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O1	0.82	2.09	2.86 (1)	156
O1w—H1w···O4ⁱ	0.82	2.05	2.74 (1)	143
O1w—H2w···O3	0.82	2.15	2.82 (1)	139
O1w—H2w···O5ⁱ	0.82	2.24	2.91 (1)	139

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	2[Sn(CH₃)₂(C₆H₅)Cl(H₂O)]·C₁₀H₂₀O₅
M_r	778.91
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.8700 (3), 18.9814 (5), 9.8770 (3)
β (°)	113.636 (1)
V (Å³)	1695.2 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.67
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.534, 0.732
No. of measured, independent and observed [I > 2σ(I)] reflections	16379, 3869, 3433
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.128, 1.06
No. of reflections	3869
No. of parameters	159
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.29, −1.14

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

Sn1—C1	2.115 (5)	Sn1—O1w	2.472 (3)
Sn1—C2	2.122 (5)	Sn1—Cl1	2.485 (1)
Sn1—C3	2.139 (4)

C1—Sn1—C2	120.2 (2)	C2—Sn1—C3	116.0 (2)
C1—Sn1—C3	121.1 (2)	O1w—Sn1—Cl1	176.1 (1)

Acknowledgements

We thank Shahid Beheshti University, Heilongjiang University and the University of Malaya for supporting this work.

References

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