Dichlorido{μ3-6,6′-dieth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}octa­methyldi-μ3-oxido-tetra­tin(IV)

Lee, S.M.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809032255

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1103-m1104

doi:10.1107/S1600536809032255

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Dichlorido{μ₃-6,6′-diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}octamethyldi-μ₃-oxido-tetratin(IV)

See Mun Lee,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 6 August 2009; accepted 14 August 2009; online 19 August 2009)

In the title tetranuclear tin(IV) complex, [Sn₄(CH₃)₈(C₂₀H₂₂N₂O₄)Cl₂O₂], there are three completely different tin-atom coordinations. One metal atom (site symmetry 2) adopts a distorted pentagonal-bipyramidal SnC₂N₂O₃ coordination arising from the N,N′,O,O′-tetradentate deprotonated Schiff base, two methyl groups in the axial sites and a μ₃-O atom that also bonds to two further Sn atoms. Two symmetry-equivalent Sn atoms adopt very distorted SnC₂O₄ arrangements that could be described as pentagonal-bipyramidal with one equatorial vertex missing and the C atoms in the axial site. The final Sn atom (site symmetry 2) adopts an SnC₂Cl₂O trigonal-bipyramidal arrangement, with Cl atoms in the axial sites. As well as the two Sn atoms, one O atom lies on a twofold rotation rotation axis, and another is disordered about the axis. The terminal ethoxy group is disordered over two sets of sites with equal occupancy.

Related literature

For other organotin derivatives of 6,6′-dialkoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenol, see: Cunningham et al. (2004 ). For the crystal structure of 6,6′-diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenol, see: Bermejo et al. (2007 ).

Experimental

Crystal data

[Sn₄(CH₃)₈(C₂₀H₂₂N₂O₄)Cl₂O₂]
M_r = 1052.33
Tetragonal, P 4₃ 2₁ 2
a = 9.8723 (1) Å
c = 38.0217 (5) Å
V = 3705.68 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 100 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.863, T_max = 1.000 (expected range = 0.563–0.652)
68779 measured reflections
4259 independent reflections
4089 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.072
S = 1.07
4259 reflections
198 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.69 e Å⁻³
Absolute structure: Flack (1983 ), 1694 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Selected geometric parameters (Å, °)

Sn1—O3	2.072 (4)
Sn1—C1	2.112 (5)
Sn1—O1	2.410 (3)
Sn1—N1	2.426 (4)
Sn2—O1	2.463 (3)
Sn2—O2	2.791 (4)
Sn2—O3	2.006 (2)
Sn2—C2	2.091 (5)
Sn2—C3	2.100 (5)
Sn2—O4	2.125 (17)
Sn3—O4	1.964 (5)
Sn3—C4	2.114 (5)
Sn3—Cl1	2.5829 (15)

C1ⁱ—Sn1—C1	173.9 (3)
C2—Sn2—C3	147.8 (2)
C4—Sn3—C4ⁱ	132.6 (3)
Symmetry code: (i) y, x, -z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032255/hb5035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032255/hb5035Isup2.hkl

checkCIF report

Related literature top

For other organotin derivatives of 6,6'-dialkoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenol, see: Cunningham et al. (2004). For the crystal structure of 6,6'-diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenol, see: Bermejo et al. (2007).

Experimental top

One mmol (0.36 g) of the Schiff base was synthesized in toluene according to a literature procedure (Bermejo et al., 2007) from 3-ethoxysalicylaldehyde and ethylenediamine. To the solution was added an excess of triethylamine (0.5 ml). A toluene solution of dimethyltin dichloride (0.20 g, 1 mmol) was added and the mixture heated. Yellow blocks of (I) were isolated from the cool filtered solution.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. View of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the ethyl groups are not shown. Unlabelled atoms are generated by the symmetry operation (y, x, –z).

Dichlorido{µ₃-6,6'-diethoxy-2,2'-[ethane-1,2- diylbis(nitrilomethylidyne)]diphenolato}octamethyldi-µ₃-oxido-tetratin(IV) top

Crystal data top

[Sn₄(CH₃)₈(C₂₀H₂₂N₂O₄)Cl₂O₂]	D_x = 1.886 Mg m⁻³
M_r = 1052.33	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃2₁2	Cell parameters from 9779 reflections
Hall symbol: P4 nw 2abw	θ = 2.1–26.5°
a = 9.8723 (1) Å	µ = 2.85 mm⁻¹
c = 38.0217 (5) Å	T = 100 K
V = 3705.68 (6) Å³	Block, yellow
Z = 4	0.20 × 0.18 × 0.15 mm
F(000) = 2040

Data collection top

Bruker SMART APEX diffractometer	4259 independent reflections
Radiation source: fine-focus sealed tube	4089 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.863, T_max = 1.000	k = −12→12
68779 measured reflections	l = −49→48

Refinement top

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)] = 0.027	H-atom parameters constrained
wR(F²) = 0.072	w = 1/[σ²(F_o²) + (0.0361P)² + 5.6973P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4259 reflections	Δρ_max = 0.42 e Å⁻³
198 parameters	Δρ_min = −0.69 e Å⁻³
10 restraints	Absolute structure: Flack (1983), 1694 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (4)

Crystal data top

[Sn₄(CH₃)₈(C₂₀H₂₂N₂O₄)Cl₂O₂]	Z = 4
M_r = 1052.33	Mo Kα radiation
Tetragonal, P4₃2₁2	µ = 2.85 mm⁻¹
a = 9.8723 (1) Å	T = 100 K
c = 38.0217 (5) Å	0.20 × 0.18 × 0.15 mm
V = 3705.68 (6) Å³

Data collection top

Bruker SMART APEX diffractometer	4259 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4089 reflections with I > 2σ(I)
T_min = 0.863, T_max = 1.000	R_int = 0.029
68779 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.072	Δρ_max = 0.42 e Å⁻³
S = 1.07	Δρ_min = −0.69 e Å⁻³
4259 reflections	Absolute structure: Flack (1983), 1694 Friedel pairs
198 parameters	Absolute structure parameter: 0.00 (4)
10 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.17065 (3)	0.17065 (3)	0.0000	0.05087 (13)
Sn2	0.33507 (3)	0.46713 (3)	0.035901 (8)	0.04062 (9)
Sn3	0.64067 (3)	0.64067 (3)	0.0000	0.03517 (10)
Cl1	0.51581 (18)	0.74108 (17)	0.05370 (4)	0.0693 (4)
O1	0.1449 (3)	0.3159 (3)	0.05051 (8)	0.0476 (8)
O2	0.1753 (4)	0.5180 (4)	0.09499 (11)	0.0663 (11)
O3	0.3190 (3)	0.3190 (3)	0.0000	0.0383 (9)
O4	0.5075 (16)	0.4933 (15)	0.0032 (5)	0.027 (2)	0.50
N1	−0.0212 (4)	0.0806 (4)	0.03231 (12)	0.0486 (10)
C1	0.2924 (5)	0.0328 (5)	0.02834 (14)	0.0505 (12)
H1A	0.3582	−0.0091	0.0124	0.076*
H1B	0.2350	−0.0376	0.0387	0.076*
H1C	0.3406	0.0811	0.0471	0.076*
C2	0.4546 (6)	0.3956 (6)	0.07732 (13)	0.0564 (13)
H2A	0.5248	0.3352	0.0680	0.085*
H2B	0.3977	0.3457	0.0940	0.085*
H2C	0.4974	0.4723	0.0893	0.085*
C3	0.2074 (5)	0.6200 (5)	0.01652 (15)	0.0509 (12)
H3A	0.2616	0.7000	0.0105	0.076*
H3B	0.1406	0.6441	0.0345	0.076*
H3C	0.1606	0.5873	−0.0045	0.076*
C4	0.8115 (6)	0.5917 (6)	0.03104 (17)	0.0613 (15)
H4A	0.8022	0.4991	0.0400	0.092*
H4B	0.8177	0.6549	0.0508	0.092*
H4C	0.8936	0.5983	0.0167	0.092*
C5	−0.0612 (6)	−0.0545 (6)	0.01965 (15)	0.0645 (16)
H5A	−0.1547	−0.0747	0.0275	0.077*
H5B	−0.0002	−0.1237	0.0299	0.077*
C6	−0.0948 (5)	0.1346 (5)	0.05572 (13)	0.0465 (11)
H6	−0.1747	0.0862	0.0617	0.056*
C7	−0.0736 (5)	0.2594 (5)	0.07448 (12)	0.0418 (10)
C8	−0.1778 (5)	0.2942 (6)	0.09830 (14)	0.0509 (12)
H8	−0.2577	0.2406	0.0992	0.061*
C9	−0.1654 (6)	0.4048 (6)	0.12023 (14)	0.0575 (14)
H9	−0.2372	0.4286	0.1357	0.069*
C10	−0.0475 (6)	0.4810 (6)	0.11964 (12)	0.0551 (14)
H10	−0.0369	0.5548	0.1354	0.066*
C11	0.0529 (5)	0.4504 (5)	0.09661 (12)	0.0452 (11)
C12	0.0447 (5)	0.3385 (5)	0.07272 (11)	0.0399 (9)
C13	0.2125 (16)	0.6125 (10)	0.1229 (3)	0.061 (2)*	0.50
H13A	0.3109	0.6070	0.1276	0.073*	0.50
H13B	0.1633	0.5900	0.1448	0.073*	0.50
C14	0.1759 (17)	0.7520 (13)	0.1109 (4)	0.080 (3)*	0.50
H14A	0.0782	0.7565	0.1065	0.120*	0.50
H14B	0.2252	0.7734	0.0893	0.120*	0.50
H14C	0.2001	0.8174	0.1293	0.120*	0.50
C13'	0.1933 (14)	0.6412 (9)	0.1157 (3)	0.061 (2)*	0.50
H13C	0.2913	0.6628	0.1162	0.073*	0.50
H13D	0.1656	0.6214	0.1402	0.073*	0.50
C14'	0.1189 (16)	0.7656 (14)	0.1039 (5)	0.080 (3)*	0.50
H14D	0.1808	0.8246	0.0908	0.120*	0.50
H14E	0.0841	0.8141	0.1245	0.120*	0.50
H14F	0.0432	0.7393	0.0887	0.120*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03415 (14)	0.03415 (14)	0.0843 (3)	−0.00937 (17)	−0.01282 (18)	0.01282 (18)
Sn2	0.04630 (18)	0.03956 (16)	0.03599 (14)	0.01171 (13)	0.00052 (13)	−0.00805 (12)
Sn3	0.03041 (12)	0.03041 (12)	0.0447 (2)	−0.00586 (15)	−0.00722 (12)	0.00722 (12)
Cl1	0.0783 (10)	0.0730 (10)	0.0567 (8)	0.0163 (8)	−0.0115 (7)	−0.0226 (7)
O1	0.0442 (18)	0.0470 (19)	0.0516 (18)	−0.0007 (16)	0.0139 (15)	−0.0160 (15)
O2	0.066 (3)	0.068 (3)	0.065 (2)	−0.014 (2)	0.014 (2)	−0.035 (2)
O3	0.0332 (13)	0.0332 (13)	0.049 (2)	−0.0092 (17)	0.0115 (14)	−0.0115 (14)
O4	0.031 (4)	0.022 (3)	0.029 (5)	−0.004 (3)	−0.006 (3)	0.005 (3)
N1	0.048 (2)	0.039 (2)	0.059 (2)	−0.0105 (17)	0.012 (2)	−0.0063 (19)
C1	0.052 (3)	0.039 (2)	0.061 (3)	0.004 (2)	−0.007 (2)	0.008 (2)
C2	0.058 (3)	0.067 (3)	0.044 (2)	0.004 (3)	−0.007 (2)	0.013 (2)
C3	0.042 (3)	0.041 (3)	0.070 (3)	0.009 (2)	−0.003 (2)	−0.001 (2)
C4	0.044 (3)	0.061 (3)	0.079 (4)	−0.004 (2)	−0.027 (3)	0.011 (3)
C5	0.054 (3)	0.050 (3)	0.090 (4)	−0.023 (2)	0.024 (3)	−0.014 (3)
C6	0.040 (2)	0.049 (3)	0.051 (3)	−0.004 (2)	0.008 (2)	0.006 (2)
C7	0.046 (3)	0.044 (3)	0.035 (2)	0.0085 (19)	0.0034 (19)	0.0063 (19)
C8	0.044 (3)	0.058 (3)	0.051 (3)	0.007 (2)	0.008 (2)	0.008 (2)
C9	0.060 (3)	0.070 (4)	0.043 (3)	0.017 (3)	0.015 (3)	0.003 (2)
C10	0.070 (4)	0.059 (3)	0.036 (2)	0.018 (3)	0.006 (2)	−0.007 (2)
C11	0.051 (3)	0.049 (3)	0.035 (2)	0.009 (2)	0.006 (2)	−0.004 (2)
C12	0.041 (2)	0.048 (3)	0.0302 (19)	0.009 (2)	0.0041 (17)	0.0026 (19)

Geometric parameters (Å, º) top

Sn1—O3	2.072 (4)	C2—H2B	0.9800
Sn1—C1ⁱ	2.112 (5)	C2—H2C	0.9800
Sn1—C1	2.112 (5)	C3—H3A	0.9800
Sn1—O1	2.410 (3)	C3—H3B	0.9800
Sn1—O1ⁱ	2.410 (3)	C3—H3C	0.9800
Sn1—N1ⁱ	2.426 (4)	C4—H4A	0.9800
Sn1—N1	2.426 (4)	C4—H4B	0.9800
Sn2—Cl1	3.310 (2)	C4—H4C	0.9800
Sn2—O1	2.463 (3)	C5—C5ⁱ	1.497 (12)
Sn2—O2	2.791 (4)	C5—H5A	0.9900
Sn2—O3	2.006 (2)	C5—H5B	0.9900
Sn2—C2	2.091 (5)	C6—C7	1.439 (7)
Sn2—C3	2.100 (5)	C6—H6	0.9500
Sn2—O4	2.125 (17)	C7—C12	1.406 (7)
Sn2—O4ⁱ	2.192 (16)	C7—C8	1.414 (7)
Sn2—Sn2ⁱ	3.2943 (6)	C8—C9	1.379 (8)
Sn3—O4	1.964 (5)	C8—H8	0.9500
Sn3—O4ⁱ	1.964 (5)	C9—C10	1.386 (9)
Sn3—C4	2.114 (5)	C9—H9	0.9500
Sn3—C4ⁱ	2.114 (5)	C10—C11	1.356 (7)
Sn3—Cl1	2.5829 (15)	C10—H10	0.9500
Sn3—Cl1ⁱ	2.5829 (15)	C11—C12	1.432 (7)
O1—C12	1.320 (5)	C13—C14	1.493 (9)
O2—C11	1.381 (7)	C13—H13A	0.9900
O2—C13	1.459 (8)	C13—H13B	0.9900
O2—C13'	1.460 (8)	C14—H14A	0.9800
O3—Sn2ⁱ	2.006 (2)	C14—H14B	0.9800
O4—O4ⁱ	0.31 (4)	C14—H14C	0.9800
O4—Sn2ⁱ	2.192 (16)	C13'—C14'	1.499 (9)
N1—C6	1.267 (6)	C13'—H13C	0.9900
N1—C5	1.472 (6)	C13'—H13D	0.9900
C1—H1A	0.9800	C14'—H14D	0.9800
C1—H1B	0.9800	C14'—H14E	0.9800
C1—H1C	0.9800	C14'—H14F	0.9800
C2—H2A	0.9800

O3—Sn1—C1ⁱ	93.05 (15)	C6—N1—Sn1	130.5 (3)
O3—Sn1—C1	93.04 (15)	C5—N1—Sn1	112.1 (3)
C1ⁱ—Sn1—C1	173.9 (3)	Sn1—C1—H1A	109.5
O3—Sn1—O1	69.76 (8)	Sn1—C1—H1B	109.5
C1ⁱ—Sn1—O1	89.99 (17)	H1A—C1—H1B	109.5
C1—Sn1—O1	92.12 (17)	Sn1—C1—H1C	109.5
O3—Sn1—O1ⁱ	69.76 (8)	H1A—C1—H1C	109.5
C1ⁱ—Sn1—O1ⁱ	92.12 (17)	H1B—C1—H1C	109.5
C1—Sn1—O1ⁱ	89.99 (17)	Sn2—C2—H2A	109.5
O1—Sn1—O1ⁱ	139.52 (16)	Sn2—C2—H2B	109.5
O3—Sn1—N1ⁱ	144.20 (10)	H2A—C2—H2B	109.5
C1ⁱ—Sn1—N1ⁱ	87.14 (19)	Sn2—C2—H2C	109.5
C1—Sn1—N1ⁱ	87.92 (18)	H2A—C2—H2C	109.5
O1—Sn1—N1ⁱ	146.01 (13)	H2B—C2—H2C	109.5
O1ⁱ—Sn1—N1ⁱ	74.46 (13)	Sn2—C3—H3A	109.5
O3—Sn1—N1	144.20 (10)	Sn2—C3—H3B	109.5
C1ⁱ—Sn1—N1	87.92 (18)	H3A—C3—H3B	109.5
C1—Sn1—N1	87.14 (19)	Sn2—C3—H3C	109.5
O1—Sn1—N1	74.46 (13)	H3A—C3—H3C	109.5
O1ⁱ—Sn1—N1	146.01 (13)	H3B—C3—H3C	109.5
N1ⁱ—Sn1—N1	71.6 (2)	Sn3—C4—H4A	109.5
O3—Sn2—C2	108.10 (17)	Sn3—C4—H4B	109.5
O3—Sn2—C3	103.75 (16)	H4A—C4—H4B	109.5
C2—Sn2—C3	147.8 (2)	Sn3—C4—H4C	109.5
O3—Sn2—O4	75.7 (4)	H4A—C4—H4C	109.5
C2—Sn2—O4	91.7 (5)	H4B—C4—H4C	109.5
C3—Sn2—O4	100.8 (5)	N1—C5—C5ⁱ	110.7 (4)
O3—Sn2—O4ⁱ	74.2 (4)	N1—C5—H5A	109.5
C2—Sn2—O4ⁱ	99.8 (5)	C5ⁱ—C5—H5A	109.5
C3—Sn2—O4ⁱ	93.4 (5)	N1—C5—H5B	109.5
O4—Sn2—O4ⁱ	8.1 (10)	C5ⁱ—C5—H5B	109.5
O3—Sn2—O1	69.60 (11)	H5A—C5—H5B	108.1
C2—Sn2—O1	93.19 (18)	N1—C6—C7	128.7 (5)
C3—Sn2—O1	93.30 (17)	N1—C6—H6	115.7
O4—Sn2—O1	144.8 (4)	C7—C6—H6	115.7
O4ⁱ—Sn2—O1	143.8 (4)	C12—C7—C8	120.0 (5)
O3—Sn2—Sn2ⁱ	34.82 (9)	C12—C7—C6	125.0 (4)
C2—Sn2—Sn2ⁱ	105.49 (17)	C8—C7—C6	114.8 (5)
C3—Sn2—Sn2ⁱ	103.37 (16)	C9—C8—C7	121.0 (5)
O4—Sn2—Sn2ⁱ	41.0 (4)	C9—C8—H8	119.5
O4ⁱ—Sn2—Sn2ⁱ	39.5 (4)	C7—C8—H8	119.5
O1—Sn2—Sn2ⁱ	104.40 (7)	C8—C9—C10	119.6 (5)
O4—Sn3—O4ⁱ	9.1 (10)	C8—C9—H9	120.2
O4—Sn3—C4	109.3 (6)	C10—C9—H9	120.2
O4ⁱ—Sn3—C4	118.2 (6)	C11—C10—C9	120.2 (5)
O4—Sn3—C4ⁱ	118.2 (6)	C11—C10—H10	119.9
O4ⁱ—Sn3—C4ⁱ	109.3 (6)	C9—C10—H10	119.9
C4—Sn3—C4ⁱ	132.6 (3)	C10—C11—O2	124.1 (5)
O4—Sn3—Cl1	85.2 (6)	C10—C11—C12	122.6 (5)
O4ⁱ—Sn3—Cl1	87.2 (6)	O2—C11—C12	113.2 (4)
C4—Sn3—Cl1	91.55 (19)	O1—C12—C7	124.0 (4)
C4ⁱ—Sn3—Cl1	91.49 (19)	O1—C12—C11	119.6 (4)
O4—Sn3—Cl1ⁱ	87.2 (6)	C7—C12—C11	116.4 (4)
O4ⁱ—Sn3—Cl1ⁱ	85.2 (6)	O2—C13—C14	108.0 (10)
C4—Sn3—Cl1ⁱ	91.49 (19)	O2—C13—H13A	110.1
C4ⁱ—Sn3—Cl1ⁱ	91.55 (19)	C14—C13—H13A	110.1
Cl1—Sn3—Cl1ⁱ	172.42 (8)	O2—C13—H13B	110.1
C12—O1—Sn1	133.6 (3)	C14—C13—H13B	110.1
C12—O1—Sn2	127.8 (3)	H13A—C13—H13B	108.4
Sn1—O1—Sn2	95.76 (11)	O2—C13'—C14'	117.5 (10)
C11—O2—C13	119.8 (7)	O2—C13'—H13C	107.9
C11—O2—C13'	119.0 (7)	C14'—C13'—H13C	107.9
Sn2—O3—Sn2ⁱ	110.36 (18)	O2—C13'—H13D	107.9
Sn2—O3—Sn1	124.82 (9)	C14'—C13'—H13D	107.9
Sn2ⁱ—O3—Sn1	124.82 (9)	H13C—C13'—H13D	107.2
O4ⁱ—O4—Sn3	85.4 (5)	C13'—C14'—H14D	109.5
O4ⁱ—O4—Sn2	98 (6)	C13'—C14'—H14E	109.5
Sn3—O4—Sn2	131.5 (10)	H14D—C14'—H14E	109.5
O4ⁱ—O4—Sn2ⁱ	73 (6)	C13'—C14'—H14F	109.5
Sn3—O4—Sn2ⁱ	127.4 (9)	H14D—C14'—H14F	109.5
Sn2—O4—Sn2ⁱ	99.5 (2)	H14E—C14'—H14F	109.5
C6—N1—C5	117.2 (4)

O3—Sn1—O1—C12	162.8 (4)	O3—Sn2—O4—O4ⁱ	78 (5)
C1ⁱ—Sn1—O1—C12	69.6 (4)	C2—Sn2—O4—O4ⁱ	−174 (6)
C1—Sn1—O1—C12	−104.7 (4)	C3—Sn2—O4—O4ⁱ	−23 (6)
O1ⁱ—Sn1—O1—C12	162.8 (4)	O1—Sn2—O4—O4ⁱ	88 (6)
N1ⁱ—Sn1—O1—C12	−15.3 (6)	Sn2ⁱ—Sn2—O4—O4ⁱ	75 (5)
N1—Sn1—O1—C12	−18.3 (4)	O3—Sn2—O4—Sn3	169.5 (13)
O3—Sn1—O1—Sn2	1.46 (6)	C2—Sn2—O4—Sn3	−82.3 (12)
C1ⁱ—Sn1—O1—Sn2	−91.79 (18)	C3—Sn2—O4—Sn3	67.9 (12)
C1—Sn1—O1—Sn2	93.93 (18)	O4ⁱ—Sn2—O4—Sn3	91 (6)
O1ⁱ—Sn1—O1—Sn2	1.46 (6)	O1—Sn2—O4—Sn3	179.8 (5)
N1ⁱ—Sn1—O1—Sn2	−176.7 (2)	Sn2ⁱ—Sn2—O4—Sn3	165.9 (17)
N1—Sn1—O1—Sn2	−179.63 (16)	O3—Sn2—O4—Sn2ⁱ	3.6 (5)
O3—Sn2—O1—C12	−164.5 (4)	C2—Sn2—O4—Sn2ⁱ	111.9 (6)
C2—Sn2—O1—C12	87.4 (4)	C3—Sn2—O4—Sn2ⁱ	−98.0 (6)
C3—Sn2—O1—C12	−61.0 (4)	O4ⁱ—Sn2—O4—Sn2ⁱ	−75 (5)
O4—Sn2—O1—C12	−175.1 (9)	O1—Sn2—O4—Sn2ⁱ	13.9 (13)
O4ⁱ—Sn2—O1—C12	−161.3 (9)	O3—Sn1—N1—C6	19.7 (6)
Sn2ⁱ—Sn2—O1—C12	−165.7 (3)	C1ⁱ—Sn1—N1—C6	−72.6 (5)
O3—Sn2—O1—Sn1	−1.51 (7)	C1—Sn1—N1—C6	110.9 (5)
C2—Sn2—O1—Sn1	−109.65 (19)	O1—Sn1—N1—C6	17.9 (5)
C3—Sn2—O1—Sn1	101.95 (18)	O1ⁱ—Sn1—N1—C6	−163.3 (4)
O4—Sn2—O1—Sn1	−12.1 (9)	N1ⁱ—Sn1—N1—C6	−160.3 (6)
O4ⁱ—Sn2—O1—Sn1	1.7 (9)	O3—Sn1—N1—C5	−165.8 (3)
Sn2ⁱ—Sn2—O1—Sn1	−2.76 (12)	C1ⁱ—Sn1—N1—C5	101.8 (4)
C2—Sn2—O3—Sn2ⁱ	−91.27 (17)	C1—Sn1—N1—C5	−74.6 (4)
C3—Sn2—O3—Sn2ⁱ	93.72 (16)	O1—Sn1—N1—C5	−167.6 (4)
O4—Sn2—O3—Sn2ⁱ	−4.2 (5)	O1ⁱ—Sn1—N1—C5	11.1 (5)
O4ⁱ—Sn2—O3—Sn2ⁱ	4.1 (5)	N1ⁱ—Sn1—N1—C5	14.2 (3)
O1—Sn2—O3—Sn2ⁱ	−177.87 (9)	C6—N1—C5—C5ⁱ	134.5 (6)
C2—Sn2—O3—Sn1	88.73 (17)	Sn1—N1—C5—C5ⁱ	−40.7 (7)
C3—Sn2—O3—Sn1	−86.28 (16)	C5—N1—C6—C7	174.7 (5)
O4—Sn2—O3—Sn1	175.8 (5)	Sn1—N1—C6—C7	−11.1 (8)
O4ⁱ—Sn2—O3—Sn1	−175.9 (5)	N1—C6—C7—C12	−7.7 (8)
O1—Sn2—O3—Sn1	2.13 (9)	N1—C6—C7—C8	177.8 (5)
Sn2ⁱ—Sn2—O3—Sn1	180.0	C12—C7—C8—C9	−0.4 (7)
C1ⁱ—Sn1—O3—Sn2	86.70 (15)	C6—C7—C8—C9	174.3 (5)
C1—Sn1—O3—Sn2	−93.30 (15)	C7—C8—C9—C10	−1.8 (8)
O1—Sn1—O3—Sn2	−2.17 (9)	C8—C9—C10—C11	2.7 (8)
O1ⁱ—Sn1—O3—Sn2	177.83 (9)	C9—C10—C11—O2	−177.8 (5)
N1ⁱ—Sn1—O3—Sn2	176.03 (19)	C9—C10—C11—C12	−1.5 (8)
N1—Sn1—O3—Sn2	−3.97 (19)	C13—O2—C11—C10	11.1 (9)
C1ⁱ—Sn1—O3—Sn2ⁱ	−93.30 (15)	C13'—O2—C11—C10	−8.6 (9)
C1—Sn1—O3—Sn2ⁱ	86.70 (15)	C13—O2—C11—C12	−165.5 (7)
O1—Sn1—O3—Sn2ⁱ	177.83 (9)	C13'—O2—C11—C12	174.7 (6)
O1ⁱ—Sn1—O3—Sn2ⁱ	−2.17 (9)	Sn1—O1—C12—C7	10.6 (7)
N1ⁱ—Sn1—O3—Sn2ⁱ	−3.97 (19)	Sn2—O1—C12—C7	166.8 (3)
N1—Sn1—O3—Sn2ⁱ	176.03 (19)	Sn1—O1—C12—C11	−168.7 (3)
C4—Sn3—O4—O4ⁱ	−167 (8)	Sn2—O1—C12—C11	−12.5 (6)
C4ⁱ—Sn3—O4—O4ⁱ	13 (9)	C8—C7—C12—O1	−177.7 (4)
Cl1—Sn3—O4—O4ⁱ	103 (8)	C6—C7—C12—O1	8.1 (7)
Cl1ⁱ—Sn3—O4—O4ⁱ	−77 (8)	C8—C7—C12—C11	1.6 (7)
O4ⁱ—Sn3—O4—Sn2	−97 (9)	C6—C7—C12—C11	−172.6 (5)
C4—Sn3—O4—Sn2	95.4 (12)	C10—C11—C12—O1	178.7 (5)
C4ⁱ—Sn3—O4—Sn2	−83.7 (12)	O2—C11—C12—O1	−4.6 (7)
Cl1—Sn3—O4—Sn2	5.4 (11)	C10—C11—C12—C7	−0.7 (7)
Cl1ⁱ—Sn3—O4—Sn2	−174.0 (11)	O2—C11—C12—C7	176.0 (4)
O4ⁱ—Sn3—O4—Sn2ⁱ	65 (8)	C11—O2—C13—C14	−96.5 (12)
C4—Sn3—O4—Sn2ⁱ	−102.3 (10)	C13'—O2—C13—C14	−4 (3)
C4ⁱ—Sn3—O4—Sn2ⁱ	78.6 (13)	C11—O2—C13'—C14'	−71.7 (14)
Cl1—Sn3—O4—Sn2ⁱ	167.7 (11)	C13—O2—C13'—C14'	−169 (5)
Cl1ⁱ—Sn3—O4—Sn2ⁱ	−11.7 (11)

Symmetry code: (i) y, x, −z.

Experimental details

Crystal data
Chemical formula	[Sn₄(CH₃)₈(C₂₀H₂₂N₂O₄)Cl₂O₂]
M_r	1052.33
Crystal system, space group	Tetragonal, P4₃2₁2
Temperature (K)	100
a, c (Å)	9.8723 (1), 38.0217 (5)
V (Å³)	3705.68 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.85
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.863, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	68779, 4259, 4089
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.072, 1.07
No. of reflections	4259
No. of parameters	198
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.69
Absolute structure	Flack (1983), 1694 Friedel pairs
Absolute structure parameter	0.00 (4)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected geometric parameters (Å, º) top

Sn1—O3	2.072 (4)	Sn2—C2	2.091 (5)
Sn1—C1	2.112 (5)	Sn2—C3	2.100 (5)
Sn1—O1	2.410 (3)	Sn2—O4	2.125 (17)
Sn1—N1	2.426 (4)	Sn3—O4	1.964 (5)
Sn2—O1	2.463 (3)	Sn3—C4	2.114 (5)
Sn2—O2	2.791 (4)	Sn3—Cl1	2.5829 (15)
Sn2—O3	2.006 (2)

C1ⁱ—Sn1—C1	173.9 (3)	C4—Sn3—C4ⁱ	132.6 (3)
C2—Sn2—C3	147.8 (2)

Symmetry code: (i) y, x, −z.

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

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