{4-Hy­droxy-N′-[(2-oxido-1-naphthyl-κO)methyl­idene]benzohydrazidato-κ2N′,O}dimethyl­tin(IV)

Affan, M.A.; Sam, N.B.; Ahmad, F.B.; Tiekink, E.R.T.

doi:10.1107/S1600536810027078

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m924

https://doi.org/10.1107/S1600536810027078

Open

access

{4-Hydroxy-N′-[(2-oxido-1-naphthyl-κO)methylidene]benzohydrazidato-κ²N′,O}dimethyltin(IV)

Md. Abu Affan,^a ‡ Norrihan B. Sam,^a Fasihuddin B. Ahmad ^a and Edward R. T. Tiekink ^b ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 July 2010; accepted 8 July 2010; online 14 July 2010)

Two independent but very similar molecules comprise the asymmetric unit of the title compound, [Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]. Each Sn atom is coordinated by two methyl groups and two O atoms and an N atom from the dinegative tridentate ligand. The resultant C₂NO₂ donor set defines a coordination geometry intermediate between square-pyramidal and trigonal-pyramidal, with a small tendency towards the former. Zigzag chains running along the a axis mediated by O—H⋯N hydrogen bonding characterize the crystal packing. These are connected into layers in the ab plane by a combination of C—H⋯N and π–π [centroid–centroid distances = 3.658 (2) and 3.6740 (18) Å] interactions. The layers are connected along the c axis via C—H⋯O interactions.

Related literature

For related studies on organotin compounds, see: Affan et al. (2009 ); Zukerman-Schpector et al. (2009 ). For the structure of the dichloromethane solvate of the title compound, see: Cui et al. (2007 ). For coordination geometry, see: Addison et al. (1984 ).

Experimental

Crystal data

[Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]
M_r = 453.05
Monoclinic, P 2₁ /c
a = 12.9422 (4) Å
b = 16.5264 (5) Å
c = 16.9949 (5) Å
β = 94.923 (3)°
V = 3621.59 (19) Å³
Z = 8
Mo Kα radiation
μ = 1.43 mm⁻¹
T = 150 K
0.20 × 0.15 × 0.06 mm

Data collection

Oxford Diffraction Gemini E diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.863, T_max = 1.000
12413 measured reflections
6668 independent reflections
5647 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.069
S = 1.05
6668 reflections
475 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N3ⁱ	0.84	1.91	2.749 (3)	178
O6—H6a⋯N1ⁱⁱ	0.84	1.91	2.738 (3)	167
C8—H8⋯O5ⁱⁱⁱ	0.95	2.59	3.477 (4)	155
C21—H21a⋯N1^iv	0.98	2.62	3.494 (4)	149
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z-1; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027078/bt5292sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027078/bt5292Isup2.hkl

checkCIF report

Comment top

Interest in the title compound (I) stems from on-going studies into biological and structural aspects of organotin compounds (Affan et al., 2009; Zukerman-Schpector et al., 2009). Two independent molecules comprise the crystallographic asymmetric unit of (I) with the first molecule, Fig. 1, being virtually superimposable upon the second, Fig. 2, there being only small differences in the relative orientations of aromatic rings in the molecules. The similarity between the molecules is reflected in r.m.s. values for bond distances and angles of 0.0063 Å and 1.128 °, respectively. The Sn atom environment in each case is based on a C₂NO₂ donor set provided by two methyl groups, and the NO₂ atoms of the dinegative, tridentate ligand. The coordination geometry is intermediate between square pyramidal and trigonal bipyramidal with a leaning towards the former. These assignments are based on the values calculated for τ of 0.48 and 0.43 for the Sn1 and Sn2 atoms, respectively, which compare to the τ values of 0.0 and 1.0 for ideal square pyramidal and trigonal bipyramidal geometries, respectively (Addison et al., 1984).

The crystal packing is dominated by O–H···N hydrogen bonding between the hydroxyl group and the non-coordinating imine-N atoms, Table 1. These lead to the formation of zigzag supramolecular chains along the a axis, Fig. 3. Chains are consolidated into layers via a combination of C–H···N interactions, Table 1, and π–π contacts, Fig. 4. The latter occur between centrosymmetrically related rings involving both the benzene ring and the fused ring systems, i.e. Cg(C11–C15,C20)···Cg(C35–C40)ⁱ = 3.658 (2) Å and Cg(C4–C9)···Cg(C31–C35,C40)ⁱⁱ = 3.6740 (18) Å for i: 2 - x, 1 - y, 1 - z, and ii: 1 - x, 1 - y, 1 - z. Layers thus formed stack along the c axis, being connected by C–H···O contacts, Table 1 and Fig. 5.

The molecular structures in (I) resemble closely that found in the dichloromethane solvate (Cui et al., 2007), which also has an intermediate coordination geometry but slightly distorted to trigonal bipyramidal (τ = 0.51). Interestingly, despite the presence of lattice solvent, the supramolecular zigzag chains mediated by O–H···N hydrogen bonding persist in the literature structure.

Related literature top

For related studies on organotin compounds, see: Affan et al. (2009); Zukerman-Schpector et al. (2009). For the structure of the dichloromethane solvate of the title compound, see: Cui et al. (2007). For coordination geometry, see: Addison et al. (1984).

Experimental top

2-Hydroxy-1-naphthaldehyde-4-hydroxybenzhydrazone (0.612 g, 2 mmol) was dissolved in hot absolute methanol (20 ml) in a Schlenk round bottom flask under purified nitrogen atmosphere. Then, a potassium hydroxide solution (0.224 g, 4 mmol) in absolute methanol (5 ml) was added dropwise and the colour of the resulting solution faded from yellow to light-yellow. The resulting solution was refluxed under a nitrogen atmosphere for 1 h. A solution of dimethyltin(IV) dichloride (0.439 g, 2 mmol) in absolute methanol (5 ml) was added dropwise. The resulting solution was refluxed for 4 h and allowed to cool to room temperature for 30 min. The white precipitate of potassium chloride was removed by filtration. The filtrate was evaporated to dryness using a rotary apparatus under reduced pressure. The yellow crystals obtained were washed with hexane and dried in vacuo over silica gel. Single crystals suitable for X-ray analyses were obtained from the slow evaporation of an ethanol solution at room temperature. Yield: 0.67 g, 53%, and m.pt.540–542 K.

Structure description top

For related studies on organotin compounds, see: Affan et al. (2009); Zukerman-Schpector et al. (2009). For the structure of the dichloromethane solvate of the title compound, see: Cui et al. (2007). For coordination geometry, see: Addison et al. (1984).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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 top

	Fig. 1. The molecular structure of the first independent molecule of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. The molecular structure of the second independent molecule of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 3. A view of the supramolecular chain along the a axis in (I) mediated by O–H···N hydrogen bonding shown as orange dashed lines.
	Fig. 4. A view of the 2-D supramolecular array in the ab plane in (I) with the O–H···N hydrogen bonding, C–H···N and π–π contacts shown as orange, blue and purple dashed lines, respectively.
	Fig. 5. A view in projection down the a axis of (I) showing the stacking of 2-D arrays along the c axis. The C–H···O contacts shown as brown dashed lines.

{4-Hydroxy-N'-[(2-oxido-1-naphthyl- κO)methylidene]benzohydrazidato-κ²N',O}dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]	F(000) = 1808
M_r = 453.05	D_x = 1.662 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7047 reflections
a = 12.9422 (4) Å	θ = 2.3–27.4°
b = 16.5264 (5) Å	µ = 1.43 mm⁻¹
c = 16.9949 (5) Å	T = 150 K
β = 94.923 (3)°	Prism, pink
V = 3621.59 (19) Å³	0.20 × 0.15 × 0.06 mm
Z = 8

Data collection top

Oxford Diffraction Gemini E diffractometer	6668 independent reflections
Radiation source: fine-focus sealed tube	5647 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.5081 pixels mm^-1	θ_max = 25.5°, θ_min = 2.3°
ω scans	h = −15→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −19→19
T_min = 0.863, T_max = 1.000	l = −20→19
12413 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0238P)² + 0.8497P] where P = (F_o² + 2F_c²)/3
6668 reflections	(Δ/σ)_max = 0.001
475 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]	V = 3621.59 (19) Å³
M_r = 453.05	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9422 (4) Å	µ = 1.43 mm⁻¹
b = 16.5264 (5) Å	T = 150 K
c = 16.9949 (5) Å	0.20 × 0.15 × 0.06 mm
β = 94.923 (3)°

Data collection top

Oxford Diffraction Gemini E diffractometer	6668 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	5647 reflections with I > 2σ(I)
T_min = 0.863, T_max = 1.000	R_int = 0.027
12413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	Δρ_max = 0.73 e Å⁻³
6668 reflections	Δρ_min = −0.51 e Å⁻³
475 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.372807 (18)	0.439312 (13)	0.384468 (13)	0.01894 (7)
O1	0.22567 (17)	0.48447 (13)	0.33302 (12)	0.0229 (5)
O2	0.51368 (18)	0.37879 (14)	0.38188 (13)	0.0280 (6)
O3	−0.09090 (17)	0.69902 (13)	0.11649 (13)	0.0226 (5)
H3	−0.1239	0.7217	0.1508	0.034*
N1	0.2992 (2)	0.47633 (15)	0.21448 (15)	0.0159 (6)
N2	0.3766 (2)	0.43266 (15)	0.25829 (15)	0.0158 (6)
C1	0.3054 (3)	0.3524 (2)	0.4554 (2)	0.0308 (9)
H1A	0.2763	0.3082	0.4220	0.046*
H1B	0.2502	0.3778	0.4827	0.046*
H1C	0.3585	0.3308	0.4944	0.046*
C2	0.4287 (3)	0.55396 (19)	0.4238 (2)	0.0271 (8)
H2A	0.4204	0.5597	0.4803	0.041*
H2B	0.3893	0.5965	0.3945	0.041*
H2C	0.5022	0.5587	0.4149	0.041*
C3	0.2257 (2)	0.50146 (18)	0.25852 (18)	0.0162 (7)
C4	0.1430 (2)	0.55217 (18)	0.22049 (18)	0.0152 (7)
C5	0.0645 (2)	0.58043 (18)	0.26549 (19)	0.0171 (7)
H5	0.0652	0.5660	0.3196	0.021*
C6	−0.0138 (2)	0.62907 (19)	0.23155 (18)	0.0181 (7)
H6	−0.0666	0.6478	0.2626	0.022*
C7	−0.0163 (2)	0.65090 (19)	0.15242 (19)	0.0181 (7)
C8	0.0604 (2)	0.6219 (2)	0.10710 (19)	0.0215 (8)
H8	0.0593	0.6360	0.0528	0.026*
C9	0.1378 (2)	0.57307 (19)	0.14092 (19)	0.0202 (7)
H9	0.1891	0.5530	0.1092	0.024*
C10	0.4458 (2)	0.39988 (18)	0.21694 (18)	0.0160 (7)
H10	0.4339	0.4055	0.1613	0.019*
C11	0.5367 (2)	0.35692 (18)	0.24451 (19)	0.0169 (7)
C12	0.5666 (3)	0.34850 (19)	0.32603 (19)	0.0190 (7)
C13	0.6590 (3)	0.30561 (18)	0.3504 (2)	0.0224 (8)
H13	0.6788	0.2995	0.4052	0.027*
C14	0.7193 (3)	0.27336 (19)	0.2977 (2)	0.0226 (8)
H14	0.7804	0.2450	0.3162	0.027*
C15	0.6935 (3)	0.28078 (18)	0.2147 (2)	0.0193 (7)
C16	0.7574 (3)	0.24726 (19)	0.1600 (2)	0.0259 (8)
H16	0.8183	0.2187	0.1789	0.031*
C17	0.7338 (3)	0.2550 (2)	0.0806 (2)	0.0334 (9)
H17	0.7775	0.2318	0.0445	0.040*
C18	0.6446 (3)	0.2973 (2)	0.0530 (2)	0.0365 (10)
H18	0.6282	0.3035	−0.0022	0.044*
C19	0.5802 (3)	0.3301 (2)	0.1050 (2)	0.0308 (9)
H19	0.5194	0.3581	0.0849	0.037*
C20	0.6022 (3)	0.32324 (18)	0.18701 (19)	0.0188 (7)
Sn2	0.863063 (17)	0.698292 (13)	0.901481 (13)	0.01777 (7)
O4	0.72509 (17)	0.75323 (13)	0.84463 (12)	0.0234 (5)
O5	0.99479 (18)	0.62575 (14)	0.90442 (13)	0.0291 (6)
O6	0.40545 (17)	0.94156 (14)	0.60703 (13)	0.0240 (5)
H6A	0.3654	0.9612	0.6384	0.036*
N3	0.79687 (19)	0.72937 (15)	0.72772 (15)	0.0150 (6)
N4	0.8715 (2)	0.68727 (14)	0.77582 (15)	0.0150 (6)
C21	0.7751 (3)	0.6187 (2)	0.96517 (19)	0.0261 (8)
H21A	0.7460	0.5760	0.9299	0.039*
H21B	0.7187	0.6486	0.9869	0.039*
H21C	0.8196	0.5944	1.0084	0.039*
C22	0.9403 (3)	0.80532 (19)	0.9414 (2)	0.0290 (9)
H22A	0.9540	0.8034	0.9990	0.043*
H22B	0.8966	0.8523	0.9266	0.043*
H22C	1.0061	0.8099	0.9171	0.043*
C23	0.7252 (2)	0.76115 (18)	0.76921 (19)	0.0167 (7)
C24	0.6415 (2)	0.80870 (17)	0.72659 (18)	0.0151 (7)
C25	0.5548 (2)	0.83069 (18)	0.76511 (19)	0.0166 (7)
H25	0.5506	0.8156	0.8187	0.020*
C26	0.4749 (2)	0.87418 (18)	0.72596 (19)	0.0189 (7)
H26	0.4157	0.8880	0.7526	0.023*
C27	0.4805 (2)	0.89776 (19)	0.64805 (19)	0.0175 (7)
C28	0.5677 (2)	0.8776 (2)	0.60977 (19)	0.0210 (8)
H28	0.5731	0.8950	0.5570	0.025*
C29	0.6457 (2)	0.83292 (19)	0.64771 (19)	0.0196 (7)
H29	0.7037	0.8180	0.6203	0.023*
C30	0.9417 (2)	0.65032 (17)	0.73749 (19)	0.0166 (7)
H30	0.9319	0.6528	0.6815	0.020*
C31	1.0306 (2)	0.60716 (18)	0.76933 (19)	0.0165 (7)
C32	1.0538 (3)	0.59785 (19)	0.8512 (2)	0.0226 (8)
C33	1.1456 (3)	0.55688 (19)	0.8799 (2)	0.0274 (8)
H33	1.1609	0.5505	0.9353	0.033*
C34	1.2119 (3)	0.52668 (19)	0.8300 (2)	0.0278 (9)
H34	1.2737	0.5008	0.8511	0.033*
C35	1.1910 (3)	0.53289 (18)	0.7467 (2)	0.0230 (8)
C36	1.2606 (3)	0.49950 (19)	0.6957 (2)	0.0288 (9)
H36	1.3221	0.4735	0.7171	0.035*
C37	1.2394 (3)	0.5046 (2)	0.6157 (2)	0.0359 (10)
H37	1.2868	0.4824	0.5818	0.043*
C38	1.1497 (3)	0.5418 (2)	0.5836 (2)	0.0361 (10)
H38	1.1354	0.5443	0.5279	0.043*
C39	1.0809 (3)	0.5753 (2)	0.6322 (2)	0.0263 (8)
H39	1.0195	0.6005	0.6092	0.032*
C40	1.0997 (2)	0.57292 (18)	0.7152 (2)	0.0186 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02143 (14)	0.02241 (13)	0.01285 (12)	−0.00068 (10)	0.00070 (10)	−0.00022 (10)
O1	0.0201 (13)	0.0329 (13)	0.0160 (12)	0.0038 (11)	0.0031 (10)	0.0017 (11)
O2	0.0300 (14)	0.0385 (14)	0.0150 (12)	0.0083 (12)	−0.0013 (11)	0.0023 (11)
O3	0.0174 (13)	0.0313 (13)	0.0193 (12)	0.0065 (11)	0.0023 (10)	−0.0044 (11)
N1	0.0128 (14)	0.0185 (14)	0.0163 (14)	0.0014 (12)	0.0005 (12)	−0.0022 (12)
N2	0.0137 (14)	0.0180 (14)	0.0151 (14)	−0.0010 (12)	−0.0027 (12)	0.0009 (12)
C1	0.042 (2)	0.032 (2)	0.0191 (19)	−0.0061 (18)	0.0068 (18)	−0.0007 (16)
C2	0.034 (2)	0.0242 (19)	0.0220 (19)	0.0000 (16)	−0.0013 (17)	−0.0006 (16)
C3	0.0127 (17)	0.0159 (16)	0.0196 (18)	−0.0071 (14)	−0.0001 (14)	−0.0061 (14)
C4	0.0114 (16)	0.0177 (16)	0.0163 (17)	−0.0039 (14)	0.0009 (13)	−0.0032 (14)
C5	0.0163 (17)	0.0201 (17)	0.0151 (17)	−0.0038 (14)	0.0022 (14)	−0.0006 (14)
C6	0.0142 (17)	0.0221 (17)	0.0190 (18)	−0.0016 (14)	0.0069 (14)	−0.0031 (15)
C7	0.0105 (17)	0.0215 (18)	0.0218 (18)	0.0012 (14)	−0.0015 (14)	−0.0024 (15)
C8	0.0175 (18)	0.0322 (19)	0.0148 (17)	0.0054 (16)	0.0018 (15)	−0.0033 (15)
C9	0.0146 (17)	0.0258 (18)	0.0206 (18)	0.0014 (15)	0.0033 (15)	−0.0063 (15)
C10	0.0180 (17)	0.0166 (16)	0.0137 (16)	−0.0015 (14)	0.0026 (14)	−0.0018 (14)
C11	0.0172 (18)	0.0144 (16)	0.0186 (17)	−0.0019 (14)	−0.0012 (14)	0.0004 (14)
C12	0.0191 (18)	0.0180 (17)	0.0197 (18)	−0.0006 (14)	0.0008 (15)	0.0003 (14)
C13	0.0223 (19)	0.0219 (18)	0.0219 (18)	−0.0035 (15)	−0.0053 (16)	0.0062 (15)
C14	0.0185 (19)	0.0170 (17)	0.031 (2)	0.0036 (15)	−0.0045 (16)	0.0066 (16)
C15	0.0173 (18)	0.0120 (16)	0.0276 (19)	−0.0004 (14)	−0.0037 (15)	0.0018 (15)
C16	0.0186 (19)	0.0184 (18)	0.040 (2)	0.0060 (15)	0.0003 (17)	−0.0025 (17)
C17	0.032 (2)	0.035 (2)	0.034 (2)	0.0126 (18)	0.0064 (19)	−0.0082 (18)
C18	0.041 (2)	0.050 (2)	0.0190 (19)	0.019 (2)	0.0012 (18)	−0.0046 (18)
C19	0.026 (2)	0.042 (2)	0.024 (2)	0.0161 (18)	−0.0010 (17)	−0.0065 (18)
C20	0.0185 (18)	0.0159 (17)	0.0213 (18)	−0.0012 (14)	−0.0020 (15)	−0.0028 (14)
Sn2	0.01788 (13)	0.02101 (13)	0.01475 (12)	0.00164 (10)	0.00322 (10)	0.00117 (10)
O4	0.0200 (13)	0.0354 (14)	0.0157 (12)	0.0102 (11)	0.0067 (10)	0.0035 (11)
O5	0.0279 (14)	0.0394 (14)	0.0200 (13)	0.0163 (12)	0.0025 (11)	0.0036 (11)
O6	0.0190 (13)	0.0342 (14)	0.0188 (12)	0.0109 (11)	0.0010 (10)	−0.0031 (11)
N3	0.0095 (14)	0.0184 (14)	0.0172 (14)	0.0025 (11)	0.0012 (11)	0.0008 (12)
N4	0.0137 (14)	0.0156 (13)	0.0157 (14)	0.0007 (11)	0.0016 (12)	0.0026 (11)
C21	0.036 (2)	0.0276 (19)	0.0147 (18)	−0.0106 (17)	0.0039 (16)	−0.0008 (15)
C22	0.028 (2)	0.028 (2)	0.031 (2)	−0.0085 (17)	0.0023 (18)	−0.0017 (17)
C23	0.0131 (17)	0.0148 (16)	0.0232 (18)	−0.0054 (14)	0.0072 (15)	−0.0013 (14)
C24	0.0144 (17)	0.0118 (15)	0.0195 (17)	−0.0017 (13)	0.0037 (14)	−0.0022 (14)
C25	0.0155 (17)	0.0162 (16)	0.0186 (17)	−0.0018 (14)	0.0035 (14)	−0.0024 (14)
C26	0.0133 (17)	0.0179 (17)	0.0263 (19)	−0.0028 (14)	0.0071 (15)	−0.0053 (15)
C27	0.0112 (17)	0.0197 (17)	0.0211 (18)	−0.0016 (14)	−0.0022 (14)	−0.0044 (15)
C28	0.0192 (18)	0.0302 (19)	0.0139 (17)	0.0025 (16)	0.0024 (14)	0.0002 (15)
C29	0.0140 (17)	0.0231 (17)	0.0225 (18)	0.0042 (15)	0.0067 (15)	−0.0061 (15)
C30	0.0188 (18)	0.0137 (16)	0.0180 (17)	−0.0041 (14)	0.0048 (15)	−0.0020 (14)
C31	0.0101 (16)	0.0165 (17)	0.0233 (18)	−0.0013 (13)	0.0038 (14)	−0.0008 (14)
C32	0.0220 (19)	0.0182 (17)	0.028 (2)	0.0012 (15)	0.0057 (16)	0.0027 (16)
C33	0.026 (2)	0.027 (2)	0.029 (2)	0.0046 (16)	−0.0004 (17)	0.0086 (17)
C34	0.021 (2)	0.0175 (17)	0.045 (2)	0.0058 (15)	0.0026 (18)	0.0093 (17)
C35	0.0171 (18)	0.0103 (16)	0.042 (2)	−0.0036 (14)	0.0062 (17)	0.0002 (16)
C36	0.019 (2)	0.0135 (17)	0.055 (3)	0.0025 (15)	0.0099 (19)	−0.0043 (18)
C37	0.030 (2)	0.028 (2)	0.053 (3)	0.0003 (18)	0.021 (2)	−0.018 (2)
C38	0.034 (2)	0.040 (2)	0.036 (2)	0.0026 (19)	0.012 (2)	−0.0114 (19)
C39	0.0194 (19)	0.0294 (19)	0.031 (2)	0.0020 (16)	0.0087 (17)	−0.0072 (17)
C40	0.0141 (17)	0.0136 (16)	0.0286 (19)	−0.0001 (14)	0.0051 (15)	−0.0024 (15)

Geometric parameters (Å, º) top

Sn1—O2	2.083 (2)	Sn2—O5	2.081 (2)
Sn1—C1	2.112 (3)	Sn2—C21	2.099 (3)
Sn1—C2	2.116 (3)	Sn2—C22	2.115 (3)
Sn1—N2	2.152 (2)	Sn2—N4	2.155 (2)
Sn1—O1	2.159 (2)	Sn2—O4	2.157 (2)
O1—C3	1.297 (4)	O4—C23	1.288 (4)
O2—C12	1.316 (4)	O5—C32	1.316 (4)
O3—C7	1.355 (4)	O6—C27	1.355 (4)
O3—H3	0.8400	O6—H6A	0.8400
N1—C3	1.326 (4)	N3—C23	1.321 (4)
N1—N2	1.397 (3)	N3—N4	1.396 (3)
N2—C10	1.303 (4)	N4—C30	1.314 (4)
C1—H1A	0.9800	C21—H21A	0.9800
C1—H1B	0.9800	C21—H21B	0.9800
C1—H1C	0.9800	C21—H21C	0.9800
C2—H2A	0.9800	C22—H22A	0.9800
C2—H2B	0.9800	C22—H22B	0.9800
C2—H2C	0.9800	C22—H22C	0.9800
C3—C4	1.466 (4)	C23—C24	1.477 (4)
C4—C9	1.392 (4)	C24—C25	1.395 (4)
C4—C5	1.403 (4)	C24—C29	1.405 (4)
C5—C6	1.380 (4)	C25—C26	1.382 (4)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.390 (4)	C26—C27	1.388 (4)
C6—H6	0.9500	C26—H26	0.9500
C7—C8	1.393 (4)	C27—C28	1.390 (4)
C8—C9	1.373 (4)	C28—C29	1.367 (4)
C8—H8	0.9500	C28—H28	0.9500
C9—H9	0.9500	C29—H29	0.9500
C10—C11	1.418 (4)	C30—C31	1.421 (4)
C10—H10	0.9500	C30—H30	0.9500
C11—C12	1.413 (4)	C31—C32	1.407 (5)
C11—C20	1.458 (4)	C31—C40	1.452 (4)
C12—C13	1.421 (4)	C32—C33	1.417 (5)
C13—C14	1.347 (4)	C33—C34	1.352 (4)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.427 (4)	C34—C35	1.423 (5)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.409 (4)	C35—C36	1.415 (4)
C15—C20	1.419 (4)	C35—C40	1.418 (5)
C16—C17	1.364 (5)	C36—C37	1.365 (5)
C16—H16	0.9500	C36—H36	0.9500
C17—C18	1.395 (5)	C37—C38	1.384 (5)
C17—H17	0.9500	C37—H37	0.9500
C18—C19	1.377 (5)	C38—C39	1.381 (5)
C18—H18	0.9500	C38—H38	0.9500
C19—C20	1.402 (5)	C39—C40	1.410 (5)
C19—H19	0.9500	C39—H39	0.9500

O2—Sn1—C1	95.19 (12)	O5—Sn2—C21	96.08 (12)
O2—Sn1—C2	99.24 (12)	O5—Sn2—C22	96.34 (12)
C1—Sn1—C2	125.14 (13)	C21—Sn2—C22	128.37 (13)
O2—Sn1—N2	81.92 (9)	O5—Sn2—N4	82.19 (9)
C1—Sn1—N2	125.45 (11)	C21—Sn2—N4	122.25 (11)
C2—Sn1—N2	108.92 (11)	C22—Sn2—N4	109.01 (12)
O2—Sn1—O1	154.21 (8)	O5—Sn2—O4	153.95 (9)
C1—Sn1—O1	94.20 (12)	C21—Sn2—O4	91.72 (12)
C2—Sn1—O1	94.83 (11)	C22—Sn2—O4	98.16 (12)
N2—Sn1—O1	73.08 (9)	N4—Sn2—O4	72.67 (9)
C3—O1—Sn1	113.32 (19)	C23—O4—Sn2	114.62 (19)
C12—O2—Sn1	135.1 (2)	C32—O5—Sn2	135.1 (2)
C7—O3—H3	109.5	C27—O6—H6A	109.5
C3—N1—N2	112.2 (3)	C23—N3—N4	111.6 (2)
C10—N2—N1	115.0 (3)	C30—N4—N3	114.5 (3)
C10—N2—Sn1	129.4 (2)	C30—N4—Sn2	128.8 (2)
N1—N2—Sn1	115.33 (17)	N3—N4—Sn2	116.53 (17)
Sn1—C1—H1A	109.5	Sn2—C21—H21A	109.5
Sn1—C1—H1B	109.5	Sn2—C21—H21B	109.5
H1A—C1—H1B	109.5	H21A—C21—H21B	109.5
Sn1—C1—H1C	109.5	Sn2—C21—H21C	109.5
H1A—C1—H1C	109.5	H21A—C21—H21C	109.5
H1B—C1—H1C	109.5	H21B—C21—H21C	109.5
Sn1—C2—H2A	109.5	Sn2—C22—H22A	109.5
Sn1—C2—H2B	109.5	Sn2—C22—H22B	109.5
H2A—C2—H2B	109.5	H22A—C22—H22B	109.5
Sn1—C2—H2C	109.5	Sn2—C22—H22C	109.5
H2A—C2—H2C	109.5	H22A—C22—H22C	109.5
H2B—C2—H2C	109.5	H22B—C22—H22C	109.5
O1—C3—N1	122.9 (3)	O4—C23—N3	123.5 (3)
O1—C3—C4	119.5 (3)	O4—C23—C24	118.6 (3)
N1—C3—C4	117.5 (3)	N3—C23—C24	118.0 (3)
C9—C4—C5	118.1 (3)	C25—C24—C29	118.2 (3)
C9—C4—C3	122.9 (3)	C25—C24—C23	119.6 (3)
C5—C4—C3	119.1 (3)	C29—C24—C23	122.2 (3)
C6—C5—C4	120.4 (3)	C26—C25—C24	120.6 (3)
C6—C5—H5	119.8	C26—C25—H25	119.7
C4—C5—H5	119.8	C24—C25—H25	119.7
C5—C6—C7	120.7 (3)	C25—C26—C27	120.5 (3)
C5—C6—H6	119.7	C25—C26—H26	119.8
C7—C6—H6	119.7	C27—C26—H26	119.8
O3—C7—C6	123.0 (3)	O6—C27—C26	123.1 (3)
O3—C7—C8	117.8 (3)	O6—C27—C28	117.5 (3)
C6—C7—C8	119.2 (3)	C26—C27—C28	119.3 (3)
C9—C8—C7	120.0 (3)	C29—C28—C27	120.3 (3)
C9—C8—H8	120.0	C29—C28—H28	119.8
C7—C8—H8	120.0	C27—C28—H28	119.8
C8—C9—C4	121.7 (3)	C28—C29—C24	121.1 (3)
C8—C9—H9	119.2	C28—C29—H29	119.4
C4—C9—H9	119.2	C24—C29—H29	119.4
N2—C10—C11	128.2 (3)	N4—C30—C31	128.1 (3)
N2—C10—H10	115.9	N4—C30—H30	116.0
C11—C10—H10	115.9	C31—C30—H30	116.0
C12—C11—C10	121.5 (3)	C32—C31—C30	121.9 (3)
C12—C11—C20	119.5 (3)	C32—C31—C40	119.6 (3)
C10—C11—C20	118.9 (3)	C30—C31—C40	118.5 (3)
O2—C12—C11	123.6 (3)	O5—C32—C31	123.6 (3)
O2—C12—C13	117.2 (3)	O5—C32—C33	116.7 (3)
C11—C12—C13	119.2 (3)	C31—C32—C33	119.6 (3)
C14—C13—C12	121.7 (3)	C34—C33—C32	121.2 (3)
C14—C13—H13	119.2	C34—C33—H33	119.4
C12—C13—H13	119.2	C32—C33—H33	119.4
C13—C14—C15	121.6 (3)	C33—C34—C35	121.4 (3)
C13—C14—H14	119.2	C33—C34—H34	119.3
C15—C14—H14	119.2	C35—C34—H34	119.3
C16—C15—C20	119.7 (3)	C36—C35—C40	120.3 (3)
C16—C15—C14	121.1 (3)	C36—C35—C34	120.3 (3)
C20—C15—C14	119.1 (3)	C40—C35—C34	119.4 (3)
C17—C16—C15	121.4 (3)	C37—C36—C35	120.1 (4)
C17—C16—H16	119.3	C37—C36—H36	119.9
C15—C16—H16	119.3	C35—C36—H36	119.9
C16—C17—C18	119.2 (3)	C36—C37—C38	120.6 (3)
C16—C17—H17	120.4	C36—C37—H37	119.7
C18—C17—H17	120.4	C38—C37—H37	119.7
C19—C18—C17	120.7 (3)	C39—C38—C37	120.3 (4)
C19—C18—H18	119.7	C39—C38—H38	119.8
C17—C18—H18	119.7	C37—C38—H38	119.8
C18—C19—C20	121.5 (3)	C38—C39—C40	121.4 (4)
C18—C19—H19	119.2	C38—C39—H39	119.3
C20—C19—H19	119.2	C40—C39—H39	119.3
C19—C20—C15	117.5 (3)	C39—C40—C35	117.2 (3)
C19—C20—C11	123.7 (3)	C39—C40—C31	124.1 (3)
C15—C20—C11	118.8 (3)	C35—C40—C31	118.7 (3)

O2—Sn1—O1—C3	−29.7 (3)	O5—Sn2—O4—C23	−24.6 (3)
C1—Sn1—O1—C3	−140.9 (2)	C21—Sn2—O4—C23	−132.3 (2)
C2—Sn1—O1—C3	93.3 (2)	C22—Sn2—O4—C23	98.6 (2)
N2—Sn1—O1—C3	−15.0 (2)	N4—Sn2—O4—C23	−8.9 (2)
C1—Sn1—O2—C12	120.3 (3)	C21—Sn2—O5—C32	128.0 (3)
C2—Sn1—O2—C12	−112.8 (3)	C22—Sn2—O5—C32	−102.2 (3)
N2—Sn1—O2—C12	−4.8 (3)	N4—Sn2—O5—C32	6.2 (3)
O1—Sn1—O2—C12	9.4 (4)	O4—Sn2—O5—C32	21.3 (4)
C3—N1—N2—C10	173.8 (3)	C23—N3—N4—C30	176.3 (2)
C3—N1—N2—Sn1	−12.0 (3)	C23—N3—N4—Sn2	−7.9 (3)
O2—Sn1—N2—C10	1.2 (3)	O5—Sn2—N4—C30	−2.8 (2)
C1—Sn1—N2—C10	−89.4 (3)	C21—Sn2—N4—C30	−95.1 (3)
C2—Sn1—N2—C10	98.3 (3)	C22—Sn2—N4—C30	91.2 (3)
O1—Sn1—N2—C10	−172.4 (3)	O4—Sn2—N4—C30	−175.9 (3)
O2—Sn1—N2—N1	−172.0 (2)	O5—Sn2—N4—N3	−177.9 (2)
C1—Sn1—N2—N1	97.4 (2)	C21—Sn2—N4—N3	89.8 (2)
C2—Sn1—N2—N1	−74.9 (2)	C22—Sn2—N4—N3	−83.9 (2)
O1—Sn1—N2—N1	14.45 (18)	O4—Sn2—N4—N3	8.99 (19)
Sn1—O1—C3—N1	14.9 (4)	Sn2—O4—C23—N3	8.4 (4)
Sn1—O1—C3—C4	−163.7 (2)	Sn2—O4—C23—C24	−171.2 (2)
N2—N1—C3—O1	−2.1 (4)	N4—N3—C23—O4	−0.4 (4)
N2—N1—C3—C4	176.5 (2)	N4—N3—C23—C24	179.1 (2)
O1—C3—C4—C9	179.9 (3)	O4—C23—C24—C25	−12.1 (4)
N1—C3—C4—C9	1.3 (5)	N3—C23—C24—C25	168.4 (3)
O1—C3—C4—C5	−0.8 (4)	O4—C23—C24—C29	168.0 (3)
N1—C3—C4—C5	−179.4 (3)	N3—C23—C24—C29	−11.5 (4)
C9—C4—C5—C6	−1.5 (5)	C29—C24—C25—C26	0.8 (5)
C3—C4—C5—C6	179.3 (3)	C23—C24—C25—C26	−179.1 (3)
C4—C5—C6—C7	0.0 (5)	C24—C25—C26—C27	−1.0 (5)
C5—C6—C7—O3	−179.4 (3)	C25—C26—C27—O6	−178.9 (3)
C5—C6—C7—C8	1.1 (5)	C25—C26—C27—C28	−0.4 (5)
O3—C7—C8—C9	179.9 (3)	O6—C27—C28—C29	−179.4 (3)
C6—C7—C8—C9	−0.6 (5)	C26—C27—C28—C29	2.0 (5)
C7—C8—C9—C4	−0.9 (5)	C27—C28—C29—C24	−2.2 (5)
C5—C4—C9—C8	2.0 (5)	C25—C24—C29—C28	0.8 (5)
C3—C4—C9—C8	−178.8 (3)	C23—C24—C29—C28	−179.3 (3)
N1—N2—C10—C11	175.5 (3)	N3—N4—C30—C31	175.7 (3)
Sn1—N2—C10—C11	2.3 (5)	Sn2—N4—C30—C31	0.6 (5)
N2—C10—C11—C12	−3.8 (5)	N4—C30—C31—C32	0.9 (5)
N2—C10—C11—C20	178.3 (3)	N4—C30—C31—C40	−178.2 (3)
Sn1—O2—C12—C11	4.8 (5)	Sn2—O5—C32—C31	−6.8 (5)
Sn1—O2—C12—C13	−175.5 (2)	Sn2—O5—C32—C33	172.8 (2)
C10—C11—C12—O2	0.3 (5)	C30—C31—C32—O5	2.0 (5)
C20—C11—C12—O2	178.2 (3)	C40—C31—C32—O5	−178.9 (3)
C10—C11—C12—C13	−179.3 (3)	C30—C31—C32—C33	−177.6 (3)
C20—C11—C12—C13	−1.5 (4)	C40—C31—C32—C33	1.5 (5)
O2—C12—C13—C14	−179.1 (3)	O5—C32—C33—C34	−179.4 (3)
C11—C12—C13—C14	0.6 (5)	C31—C32—C33—C34	0.3 (5)
C12—C13—C14—C15	0.1 (5)	C32—C33—C34—C35	−1.6 (5)
C13—C14—C15—C16	179.6 (3)	C33—C34—C35—C36	−178.8 (3)
C13—C14—C15—C20	0.1 (5)	C33—C34—C35—C40	1.2 (5)
C20—C15—C16—C17	0.3 (5)	C40—C35—C36—C37	−1.0 (5)
C14—C15—C16—C17	−179.2 (3)	C34—C35—C36—C37	179.1 (3)
C15—C16—C17—C18	0.3 (6)	C35—C36—C37—C38	−0.4 (5)
C16—C17—C18—C19	−0.8 (6)	C36—C37—C38—C39	0.8 (6)
C17—C18—C19—C20	0.8 (6)	C37—C38—C39—C40	0.2 (6)
C18—C19—C20—C15	−0.2 (5)	C38—C39—C40—C35	−1.6 (5)
C18—C19—C20—C11	179.9 (3)	C38—C39—C40—C31	179.8 (3)
C16—C15—C20—C19	−0.3 (5)	C36—C35—C40—C39	1.9 (5)
C14—C15—C20—C19	179.2 (3)	C34—C35—C40—C39	−178.1 (3)
C16—C15—C20—C11	179.5 (3)	C36—C35—C40—C31	−179.4 (3)
C14—C15—C20—C11	−0.9 (4)	C34—C35—C40—C31	0.6 (4)
C12—C11—C20—C19	−178.5 (3)	C32—C31—C40—C39	176.7 (3)
C10—C11—C20—C19	−0.6 (5)	C30—C31—C40—C39	−4.2 (5)
C12—C11—C20—C15	1.6 (4)	C32—C31—C40—C35	−1.9 (4)
C10—C11—C20—C15	179.5 (3)	C30—C31—C40—C35	177.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.84	1.91	2.749 (3)	178
O6—H6a···N1ⁱⁱ	0.84	1.91	2.738 (3)	167
C8—H8···O5ⁱⁱⁱ	0.95	2.59	3.477 (4)	155
C21—H21a···N1^iv	0.98	2.62	3.494 (4)	149

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x−1, y, z−1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₈H₁₂N₂O₃)]
M_r	453.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	12.9422 (4), 16.5264 (5), 16.9949 (5)
β (°)	94.923 (3)
V (Å³)	3621.59 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.20 × 0.15 × 0.06

Data collection
Diffractometer	Oxford Diffraction Gemini E
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.863, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12413, 6668, 5647
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.069, 1.05
No. of reflections	6668
No. of parameters	475
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.51

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.84	1.91	2.749 (3)	178
O6—H6a···N1ⁱⁱ	0.84	1.91	2.738 (3)	167
C8—H8···O5ⁱⁱⁱ	0.95	2.59	3.477 (4)	155
C21—H21a···N1^iv	0.98	2.62	3.494 (4)	149

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x−1, y, z−1; (iv) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: maaffan@frst.unimas.my.

Acknowledgements

We thank MOSTI (grant No. 06–01-09-SF0046), Universiti Malaysia Sarawak, and Oxford Diffraction for supporting this study.

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Affan, M. A., Foo, S. W., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031–5037. Web of Science CSD CrossRef Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cui, J., Yin, H. & Qiao, Y. (2007). Acta Cryst. E63, m3138. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.