Di-n-but­yl{4-hydr­oxy-N′-[(2-oxido-1-naphthyl-κO)methyl­ene]benzo­hydrazidato-κ2O,N′}tin(IV)

Affan, M.A.; Sam, N.; Ahmad, F.; Ng, S.W.

doi:10.1107/S1600536810014662

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m572

https://doi.org/10.1107/S1600536810014662

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Di-n-butyl{4-hydroxy-N′-[(2-oxido-1-naphthyl-κO)methylene]benzohydrazidato-κ²O,N′}tin(IV)

Md. Abu Affan,^a Norrihan Sam,^a Fasihuddin Ahmad ^a and Seik Weng Ng ^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: seikweng@um.edu.my

(Received 19 April 2010; accepted 21 April 2010; online 24 April 2010)

The deprotonated Schiff base ligand in the title compound, [Sn(C₄H₉)₂(C₁₈H₁₂N₂O₃)], O,N,O′-chelates to the Sn atom, which is five-coordinated in a cis-C₂NO₂Sn trigonal-bipyramidal environment. The apical sites are occupied by the O atoms [O—Sn—O = 155.2 (2)°]. The hydroxy group is a hydrogen-bond donor to the two-coordinate N atom of an adjacent molecule, the hydrogen-bonding interaction giving rise to a helical chain running along the c axis. The carbon atoms of the butyl chains are equally disordered over two positions.

Related literature

For the synthesis of the Schiff base, see: Cui et al. (2007 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₁₈H₁₂N₂O₃)]
M_r = 537.21
Monoclinic, P 2₁ /c
a = 11.6644 (9) Å
b = 17.2500 (14) Å
c = 12.9296 (11) Å
β = 106.793 (1)°
V = 2490.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 293 K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.678, T_max = 0.902
19289 measured reflections
4391 independent reflections
2953 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.189
S = 1.03
4391 reflections
314 parameters
78 restraints
H-atom parameters constrained
Δρ_max = 1.19 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2ⁱ	0.84	1.99	2.824 (6)	177
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810014662/bt5252sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014662/bt5252Isup2.hkl

checkCIF report

Comment top

There are numerous reports of metal complexes of the Schiff bases derived by condensing salicylaldehyde (and related compounds) with benzohydrazide (and related compounds). E)-4-Hydroxy-N'-[(2-hydroxynaphthalen-1-yl)methylene]benzohydrazide is a less studied ligand. The deprotonated Schiff-base ligand in the title compound O,N,O'-chelates to the tin atom, which is five coordinate in a cis-C₂NO₂Sn trigonal bipyramidal environment (Scheme I, Fig. 1). The apical sites are occupied by the oxgen atoms [O–Sn–O 155.2 (2) °]. Both butyl chains are disordered over two positions in a 1:1 ratio.

Related literature top

For the synthesis of the Schiff base, see: Cui et al. (2007).

Experimental top

(E)-4-Hydroxy-N'-[(2-hydroxynaphthalen-1-yl)methylene]benzohydrazide was synthesized according to a literature method (Cui et al., 2007). The compound (0.61 g, 2 mmole) was dissolved in methanol (20 ml). Potassium hydroxide (0.23 g, 4 mmol) dissolved in methanol (5 ml) was added. The orange solution was then treated with di-n-butyltin dichloride (0.61 g, 2 mmol) in methanol (10 ml). The mixture was heated for an hour. The solution was filtered. The evaporation of the solvent gave a product that was recrystallized from ether in 70% yield; m.p. 455-457 K.

Structure description top

For the synthesis of the Schiff base, see: Cui et al. (2007).

Computing details top

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of Sn(C₄H₉)₂(C₁₈H₁₂N₂O₃) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the butyl chains is not shown.

Di-n-butyl{4-hydroxy-N'-[(2-oxido-1-naphthyl- κO)methylene]benzohydrazidato-κ²O,N'}tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₁₈H₁₂N₂O₃)]	F(000) = 1096
M_r = 537.21	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4338 reflections
a = 11.6644 (9) Å	θ = 2.2–21.2°
b = 17.2500 (14) Å	µ = 1.05 mm⁻¹
c = 12.9296 (11) Å	T = 293 K
β = 106.793 (1)°	Plate, orange
V = 2490.6 (4) Å³	0.40 × 0.40 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4391 independent reflections
Radiation source: fine-focus sealed tube	2953 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.678, T_max = 0.902	k = −20→20
19289 measured reflections	l = −15→15

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0911P)² + 4.703P] where P = (F_o² + 2F_c²)/3
4391 reflections	(Δ/σ)_max = 0.001
314 parameters	Δρ_max = 1.19 e Å⁻³
78 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(C₁₈H₁₂N₂O₃)]	V = 2490.6 (4) Å³
M_r = 537.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6644 (9) Å	µ = 1.05 mm⁻¹
b = 17.2500 (14) Å	T = 293 K
c = 12.9296 (11) Å	0.40 × 0.40 × 0.10 mm
β = 106.793 (1)°

Data collection top

Bruker SMART APEX diffractometer	4391 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2953 reflections with I > 2σ(I)
T_min = 0.678, T_max = 0.902	R_int = 0.038
19289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	78 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.03	Δρ_max = 1.19 e Å⁻³
4391 reflections	Δρ_min = −1.14 e Å⁻³
314 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.23178 (5)	0.55623 (3)	0.50133 (4)	0.0893 (3)
O1	0.2190 (5)	0.4955 (4)	0.6362 (5)	0.1033 (17)
O2	0.3235 (5)	0.6123 (3)	0.4016 (4)	0.0965 (16)
O3	0.6606 (4)	0.8107 (3)	0.2051 (3)	0.0807 (13)
H3	0.6096	0.8344	0.1560	0.121*
N1	0.4181 (5)	0.5601 (2)	0.5908 (4)	0.0602 (12)
N2	0.4920 (4)	0.6041 (3)	0.5446 (3)	0.0602 (12)
C1	0.100 (2)	0.6351 (12)	0.4946 (19)	0.145 (6)	0.50
H1A	0.0795	0.6612	0.4253	0.174*	0.50
H1B	0.0285	0.6080	0.4998	0.174*	0.50
C2	0.1348 (19)	0.6952 (16)	0.584 (2)	0.161 (7)	0.50
H2A	0.2007	0.7262	0.5752	0.193*	0.50
H2B	0.1611	0.6695	0.6536	0.193*	0.50
C3	0.026 (2)	0.7481 (16)	0.5794 (19)	0.188 (7)	0.50
H3A	0.0199	0.7890	0.5266	0.226*	0.50
H3B	−0.0477	0.7180	0.5585	0.226*	0.50
C4	0.044 (3)	0.7835 (19)	0.693 (2)	0.212 (9)	0.50
H4A	−0.0208	0.8182	0.6915	0.319*	0.50
H4B	0.1183	0.8114	0.7143	0.319*	0.50
H4C	0.0457	0.7427	0.7441	0.319*	0.50
C5	0.143 (2)	0.4749 (16)	0.3952 (13)	0.108 (5)	0.50
H5A	0.1820	0.4252	0.4169	0.130*	0.50
H5B	0.0625	0.4710	0.4008	0.130*	0.50
C6	0.136 (2)	0.4884 (13)	0.2768 (13)	0.134 (6)	0.50
H6A	0.2165	0.4907	0.2693	0.161*	0.50
H6B	0.0976	0.5378	0.2536	0.161*	0.50
C7	0.066 (3)	0.4238 (13)	0.2044 (14)	0.171 (7)	0.50
H7A	−0.0101	0.4156	0.2194	0.205*	0.50
H7B	0.1109	0.3758	0.2183	0.205*	0.50
C8	0.044 (3)	0.4484 (17)	0.0853 (13)	0.189 (7)	0.50
H8A	0.0044	0.4072	0.0387	0.284*	0.50
H8B	0.1196	0.4592	0.0723	0.284*	0.50
H8C	−0.0049	0.4941	0.0711	0.284*	0.50
C1'	0.157 (2)	0.6678 (14)	0.5198 (18)	0.145 (6)	0.50
H1'A	0.2129	0.7077	0.5135	0.174*	0.50
H1'B	0.0842	0.6750	0.4606	0.174*	0.50
C2'	0.127 (2)	0.6797 (14)	0.6253 (18)	0.161 (7)	0.50
H2'A	0.1957	0.6673	0.6857	0.193*	0.50
H2'B	0.0614	0.6457	0.6282	0.193*	0.50
C3'	0.090 (2)	0.7660 (13)	0.633 (3)	0.188 (7)	0.50
H3'A	0.1350	0.7881	0.7012	0.226*	0.50
H3'B	0.1062	0.7960	0.5751	0.226*	0.50
C4'	−0.044 (2)	0.7688 (18)	0.622 (3)	0.212 (9)	0.50
H4'A	−0.0677	0.8215	0.6277	0.319*	0.50
H4'B	−0.0596	0.7387	0.6792	0.319*	0.50
H4'C	−0.0882	0.7478	0.5537	0.319*	0.50
C5'	0.175 (2)	0.4609 (16)	0.3742 (15)	0.108 (5)	0.50
H5'A	0.2417	0.4426	0.3507	0.130*	0.50
H5'B	0.1387	0.4175	0.4009	0.130*	0.50
C6'	0.082 (2)	0.5037 (12)	0.2830 (16)	0.134 (6)	0.50
H6'A	0.0244	0.5292	0.3122	0.161*	0.50
H6'B	0.1227	0.5433	0.2530	0.161*	0.50
C7'	0.0180 (18)	0.4479 (17)	0.1940 (18)	0.171 (7)	0.50
H7'A	−0.0441	0.4754	0.1404	0.205*	0.50
H7'B	−0.0196	0.4072	0.2244	0.205*	0.50
C8'	0.107 (3)	0.4120 (18)	0.140 (2)	0.189 (7)	0.50
H8'A	0.0653	0.3760	0.0852	0.284*	0.50
H8'B	0.1687	0.3852	0.1932	0.284*	0.50
H8'C	0.1418	0.4522	0.1077	0.284*	0.50
C9	0.2968 (7)	0.4704 (4)	0.7234 (6)	0.0758 (18)
C10	0.2491 (8)	0.4253 (5)	0.7944 (7)	0.095 (2)
H10	0.1672	0.4159	0.7764	0.114*
C11	0.3217 (8)	0.3965 (4)	0.8869 (7)	0.095 (2)
H11	0.2880	0.3687	0.9324	0.113*
C12	0.4480 (7)	0.4071 (4)	0.9177 (5)	0.0766 (19)
C13	0.5209 (9)	0.3732 (4)	1.0119 (6)	0.093 (2)
H13	0.4861	0.3451	1.0564	0.111*
C14	0.6389 (10)	0.3806 (5)	1.0389 (6)	0.104 (3)
H14	0.6868	0.3583	1.1022	0.124*
C15	0.6900 (9)	0.4220 (6)	0.9718 (7)	0.108 (3)
H15	0.7728	0.4269	0.9906	0.130*
C16	0.6221 (8)	0.4556 (4)	0.8790 (6)	0.086 (2)
H16	0.6591	0.4829	0.8355	0.104*
C17	0.4985 (7)	0.4495 (3)	0.8489 (5)	0.0700 (17)
C18	0.4202 (6)	0.4832 (3)	0.7504 (5)	0.0631 (15)
C19	0.4717 (6)	0.5285 (3)	0.6834 (5)	0.0628 (15)
H19	0.5539	0.5364	0.7089	0.075*
C20	0.4327 (6)	0.6281 (3)	0.4476 (4)	0.0617 (14)
C21	0.4956 (5)	0.6762 (3)	0.3855 (4)	0.0553 (13)
C22	0.6181 (6)	0.6895 (4)	0.4194 (5)	0.0657 (15)
H22	0.6644	0.6678	0.4837	0.079*
C23	0.6716 (6)	0.7344 (4)	0.3589 (5)	0.0722 (17)
H23	0.7538	0.7428	0.3828	0.087*
C24	0.6044 (5)	0.7675 (3)	0.2624 (4)	0.0607 (14)
C25	0.4824 (6)	0.7539 (3)	0.2282 (4)	0.0669 (15)
H25	0.4359	0.7749	0.1634	0.080*
C26	0.4297 (6)	0.7091 (3)	0.2900 (4)	0.0636 (14)
H26	0.3474	0.7010	0.2665	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0800 (4)	0.0953 (4)	0.0957 (4)	0.0001 (3)	0.0303 (3)	0.0250 (3)
O1	0.082 (3)	0.131 (5)	0.105 (4)	−0.013 (3)	0.038 (3)	0.027 (4)
O2	0.089 (3)	0.117 (4)	0.073 (3)	−0.031 (3)	0.008 (3)	0.024 (3)
O3	0.083 (3)	0.100 (3)	0.067 (3)	−0.003 (3)	0.034 (2)	0.021 (2)
N1	0.080 (3)	0.054 (3)	0.054 (3)	−0.003 (2)	0.031 (2)	−0.001 (2)
N2	0.082 (3)	0.057 (3)	0.047 (2)	−0.004 (2)	0.028 (2)	−0.001 (2)
C1	0.141 (10)	0.149 (9)	0.148 (8)	−0.011 (7)	0.046 (8)	0.008 (7)
C2	0.173 (9)	0.149 (10)	0.161 (11)	0.008 (7)	0.048 (8)	−0.004 (8)
C3	0.172 (11)	0.193 (11)	0.200 (10)	0.023 (8)	0.055 (9)	−0.012 (8)
C4	0.200 (13)	0.208 (12)	0.223 (11)	0.026 (9)	0.052 (9)	−0.035 (9)
C5	0.091 (9)	0.109 (8)	0.118 (6)	−0.023 (7)	0.019 (6)	0.010 (6)
C6	0.129 (11)	0.142 (8)	0.134 (6)	0.006 (8)	0.043 (7)	0.007 (6)
C7	0.168 (12)	0.181 (10)	0.154 (7)	0.003 (9)	0.032 (8)	−0.016 (7)
C8	0.191 (12)	0.194 (12)	0.168 (8)	−0.011 (9)	0.030 (8)	−0.001 (8)
C1'	0.141 (10)	0.149 (9)	0.148 (8)	−0.011 (7)	0.046 (8)	0.008 (7)
C2'	0.173 (9)	0.149 (10)	0.161 (11)	0.008 (7)	0.048 (8)	−0.004 (8)
C3'	0.172 (11)	0.193 (11)	0.200 (10)	0.023 (8)	0.055 (9)	−0.012 (8)
C4'	0.200 (13)	0.208 (12)	0.223 (11)	0.026 (9)	0.052 (9)	−0.035 (9)
C5'	0.091 (9)	0.109 (8)	0.118 (6)	−0.023 (7)	0.019 (6)	0.010 (6)
C6'	0.129 (11)	0.142 (8)	0.134 (6)	0.006 (8)	0.043 (7)	0.007 (6)
C7'	0.168 (12)	0.181 (10)	0.154 (7)	0.003 (9)	0.032 (8)	−0.016 (7)
C8'	0.191 (12)	0.194 (12)	0.168 (8)	−0.011 (9)	0.030 (8)	−0.001 (8)
C9	0.089 (5)	0.073 (4)	0.076 (4)	0.001 (4)	0.041 (4)	0.007 (3)
C10	0.102 (6)	0.100 (5)	0.100 (6)	−0.004 (4)	0.058 (5)	0.017 (4)
C11	0.128 (7)	0.081 (5)	0.097 (6)	−0.002 (5)	0.068 (5)	0.016 (4)
C12	0.120 (6)	0.056 (4)	0.066 (4)	0.008 (4)	0.047 (4)	0.005 (3)
C13	0.140 (8)	0.074 (4)	0.077 (5)	0.009 (5)	0.051 (5)	0.014 (4)
C14	0.139 (8)	0.097 (6)	0.074 (5)	0.014 (6)	0.029 (5)	0.030 (4)
C15	0.114 (7)	0.122 (7)	0.081 (5)	0.003 (5)	0.019 (5)	0.024 (5)
C16	0.110 (6)	0.081 (5)	0.072 (4)	−0.004 (4)	0.031 (4)	0.015 (3)
C17	0.105 (6)	0.045 (3)	0.071 (4)	−0.001 (3)	0.044 (4)	−0.004 (3)
C18	0.094 (5)	0.049 (3)	0.058 (3)	−0.001 (3)	0.040 (3)	−0.004 (3)
C19	0.087 (4)	0.051 (3)	0.058 (3)	0.001 (3)	0.033 (3)	−0.001 (3)
C20	0.077 (4)	0.053 (3)	0.054 (3)	−0.002 (3)	0.019 (3)	−0.005 (3)
C21	0.078 (4)	0.046 (3)	0.044 (3)	−0.003 (3)	0.020 (3)	−0.005 (2)
C22	0.070 (4)	0.077 (4)	0.052 (3)	0.008 (3)	0.020 (3)	0.010 (3)
C23	0.070 (4)	0.090 (4)	0.060 (3)	0.004 (3)	0.023 (3)	0.014 (3)
C24	0.074 (4)	0.063 (3)	0.051 (3)	0.002 (3)	0.026 (3)	0.000 (3)
C25	0.088 (5)	0.063 (3)	0.047 (3)	−0.002 (3)	0.015 (3)	0.006 (3)
C26	0.071 (4)	0.065 (3)	0.053 (3)	−0.008 (3)	0.014 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Sn1—C5	2.02 (2)	C3'—H3'B	0.9700
Sn1—C1	2.04 (2)	C4'—H4'A	0.9600
Sn1—O1	2.076 (5)	C4'—H4'B	0.9600
Sn1—O2	2.131 (5)	C4'—H4'C	0.9600
Sn1—N1	2.148 (5)	C5'—C6'	1.536 (10)
Sn1—C1'	2.16 (2)	C5'—H5'A	0.9700
Sn1—C5'	2.28 (2)	C5'—H5'B	0.9700
O1—C9	1.301 (8)	C6'—C7'	1.522 (10)
O2—C20	1.270 (7)	C6'—H6'A	0.9700
O3—C24	1.348 (7)	C6'—H6'B	0.9700
O3—H3	0.8400	C7'—C8'	1.537 (10)
N1—C19	1.300 (7)	C7'—H7'A	0.9700
N1—N2	1.404 (6)	C7'—H7'B	0.9700
N2—C20	1.312 (7)	C8'—H8'A	0.9600
C1—C2	1.518 (10)	C8'—H8'B	0.9600
C1—H1A	0.9700	C8'—H8'C	0.9600
C1—H1B	0.9700	C9—C18	1.397 (10)
C2—C3	1.554 (10)	C9—C10	1.433 (10)
C2—H2A	0.9700	C10—C11	1.344 (11)
C2—H2B	0.9700	C10—H10	0.9300
C3—C4	1.549 (10)	C11—C12	1.422 (11)
C3—H3A	0.9700	C11—H11	0.9300
C3—H3B	0.9700	C12—C13	1.396 (10)
C4—H4A	0.9600	C12—C17	1.407 (9)
C4—H4B	0.9600	C13—C14	1.325 (12)
C4—H4C	0.9600	C13—H13	0.9300
C5—C6	1.526 (10)	C14—C15	1.384 (12)
C5—H5A	0.9700	C14—H14	0.9300
C5—H5B	0.9700	C15—C16	1.362 (11)
C6—C7	1.532 (10)	C15—H15	0.9300
C6—H6A	0.9700	C16—C17	1.384 (11)
C6—H6B	0.9700	C16—H16	0.9300
C7—C8	1.546 (10)	C17—C18	1.457 (9)
C7—H7A	0.9700	C18—C19	1.422 (8)
C7—H7B	0.9700	C19—H19	0.9300
C8—H8A	0.9600	C20—C21	1.488 (8)
C8—H8B	0.9600	C21—C26	1.375 (8)
C8—H8C	0.9600	C21—C22	1.387 (8)
C1'—C2'	1.517 (10)	C22—C23	1.372 (8)
C1'—H1'A	0.9700	C22—H22	0.9300
C1'—H1'B	0.9700	C23—C24	1.390 (8)
C2'—C3'	1.562 (10)	C23—H23	0.9300
C2'—H2'A	0.9700	C24—C25	1.383 (9)
C2'—H2'B	0.9700	C25—C26	1.377 (8)
C3'—C4'	1.523 (10)	C25—H25	0.9300
C3'—H3'A	0.9700	C26—H26	0.9300

C5—Sn1—C1	101.7 (10)	C4'—C3'—H3'A	110.0
C5—Sn1—O1	94.2 (6)	C2'—C3'—H3'A	110.0
C1—Sn1—O1	97.8 (7)	C4'—C3'—H3'B	110.0
C5—Sn1—O2	98.7 (6)	C2'—C3'—H3'B	110.0
C1—Sn1—O2	100.2 (8)	H3'A—C3'—H3'B	108.4
O1—Sn1—O2	155.2 (2)	C3'—C4'—H4'A	109.5
C5—Sn1—N1	128.7 (7)	C3'—C4'—H4'B	109.5
C1—Sn1—N1	129.6 (6)	H4'A—C4'—H4'B	109.5
O1—Sn1—N1	82.56 (19)	C3'—C4'—H4'C	109.5
O2—Sn1—N1	72.85 (18)	H4'A—C4'—H4'C	109.5
C5—Sn1—C1'	123.4 (10)	H4'B—C4'—H4'C	109.5
C1—Sn1—C1'	23.5 (8)	C6'—C5'—Sn1	101.6 (13)
O1—Sn1—C1'	103.1 (6)	C6'—C5'—H5'A	111.5
O2—Sn1—C1'	87.3 (6)	Sn1—C5'—H5'A	111.5
N1—Sn1—C1'	107.0 (7)	C6'—C5'—H5'B	111.5
C5—Sn1—C5'	13.5 (11)	Sn1—C5'—H5'B	111.5
C1—Sn1—C5'	112.9 (8)	H5'A—C5'—H5'B	109.3
O1—Sn1—C5'	99.5 (6)	C7'—C6'—C5'	111.1 (9)
O2—Sn1—C5'	89.1 (7)	C7'—C6'—H6'A	109.4
N1—Sn1—C5'	116.7 (6)	C5'—C6'—H6'A	109.4
C1'—Sn1—C5'	132.7 (9)	C7'—C6'—H6'B	109.4
C9—O1—Sn1	134.0 (4)	C5'—C6'—H6'B	109.4
C20—O2—Sn1	115.1 (4)	H6'A—C6'—H6'B	108.0
C24—O3—H3	109.5	C6'—C7'—C8'	110.4 (10)
C19—N1—N2	115.3 (5)	C6'—C7'—H7'A	109.6
C19—N1—Sn1	128.7 (4)	C8'—C7'—H7'A	109.6
N2—N1—Sn1	116.0 (3)	C6'—C7'—H7'B	109.6
C20—N2—N1	111.0 (5)	C8'—C7'—H7'B	109.6
C2—C1—Sn1	112.8 (13)	H7'A—C7'—H7'B	108.1
C2—C1—H1A	109.0	C7'—C8'—H8'A	109.5
Sn1—C1—H1A	109.0	C7'—C8'—H8'B	109.5
C2—C1—H1B	109.0	H8'A—C8'—H8'B	109.5
Sn1—C1—H1B	109.0	C7'—C8'—H8'C	109.5
H1A—C1—H1B	107.8	H8'A—C8'—H8'C	109.5
C1—C2—C3	109.5 (10)	H8'B—C8'—H8'C	109.5
C1—C2—H2A	109.8	O1—C9—C18	125.0 (6)
C3—C2—H2A	109.8	O1—C9—C10	115.7 (7)
C1—C2—H2B	109.8	C18—C9—C10	119.3 (7)
C3—C2—H2B	109.8	C11—C10—C9	120.5 (8)
H2A—C2—H2B	108.2	C11—C10—H10	119.7
C4—C3—C2	108.0 (9)	C9—C10—H10	119.7
C4—C3—H3A	110.1	C10—C11—C12	122.5 (7)
C2—C3—H3A	110.1	C10—C11—H11	118.7
C4—C3—H3B	110.1	C12—C11—H11	118.7
C2—C3—H3B	110.1	C13—C12—C11	120.8 (7)
H3A—C3—H3B	108.4	C13—C12—C17	120.6 (8)
C3—C4—H4A	109.5	C11—C12—C17	118.6 (7)
C3—C4—H4B	109.5	C14—C13—C12	120.9 (7)
H4A—C4—H4B	109.5	C14—C13—H13	119.5
C3—C4—H4C	109.5	C12—C13—H13	119.5
H4A—C4—H4C	109.5	C13—C14—C15	119.2 (8)
H4B—C4—H4C	109.5	C13—C14—H14	120.4
C6—C5—Sn1	116.3 (13)	C15—C14—H14	120.4
C6—C5—H5A	108.2	C16—C15—C14	121.7 (10)
Sn1—C5—H5A	108.2	C16—C15—H15	119.2
C6—C5—H5B	108.2	C14—C15—H15	119.2
Sn1—C5—H5B	108.2	C15—C16—C17	120.6 (7)
H5A—C5—H5B	107.4	C15—C16—H16	119.7
C5—C6—C7	111.4 (10)	C17—C16—H16	119.7
C5—C6—H6A	109.3	C16—C17—C12	117.0 (7)
C7—C6—H6A	109.3	C16—C17—C18	123.7 (6)
C5—C6—H6B	109.3	C12—C17—C18	119.3 (7)
C7—C6—H6B	109.3	C9—C18—C19	121.4 (6)
H6A—C6—H6B	108.0	C9—C18—C17	119.7 (6)
C6—C7—C8	108.3 (9)	C19—C18—C17	118.9 (6)
C6—C7—H7A	110.0	N1—C19—C18	128.1 (6)
C8—C7—H7A	110.0	N1—C19—H19	116.0
C6—C7—H7B	110.0	C18—C19—H19	116.0
C8—C7—H7B	110.0	O2—C20—N2	124.1 (6)
H7A—C7—H7B	108.4	O2—C20—C21	116.8 (5)
C7—C8—H8A	109.5	N2—C20—C21	119.1 (5)
C7—C8—H8B	109.5	C26—C21—C22	118.2 (5)
H8A—C8—H8B	109.5	C26—C21—C20	118.7 (5)
C7—C8—H8C	109.5	C22—C21—C20	123.0 (5)
H8A—C8—H8C	109.5	C23—C22—C21	120.7 (5)
H8B—C8—H8C	109.5	C23—C22—H22	119.7
C2'—C1'—Sn1	115.2 (14)	C21—C22—H22	119.7
C2'—C1'—H1'A	108.5	C22—C23—C24	120.8 (6)
Sn1—C1'—H1'A	108.5	C22—C23—H23	119.6
C2'—C1'—H1'B	108.5	C24—C23—H23	119.6
Sn1—C1'—H1'B	108.5	O3—C24—C25	122.5 (5)
H1'A—C1'—H1'B	107.5	O3—C24—C23	118.9 (6)
C1'—C2'—C3'	108.8 (10)	C25—C24—C23	118.6 (5)
C1'—C2'—H2'A	109.9	C26—C25—C24	120.0 (5)
C3'—C2'—H2'A	109.9	C26—C25—H25	120.0
C1'—C2'—H2'B	109.9	C24—C25—H25	120.0
C3'—C2'—H2'B	109.9	C21—C26—C25	121.7 (6)
H2'A—C2'—H2'B	108.3	C21—C26—H26	119.1
C4'—C3'—C2'	108.5 (10)	C25—C26—H26	119.1

C5—Sn1—O1—C9	123.5 (10)	O2—Sn1—C5'—C6'	−71.1 (14)
C1—Sn1—O1—C9	−134.0 (9)	N1—Sn1—C5'—C6'	−141.4 (13)
O2—Sn1—O1—C9	2.1 (11)	C1'—Sn1—C5'—C6'	14 (2)
N1—Sn1—O1—C9	−4.9 (7)	Sn1—C5'—C6'—C7'	−172.0 (14)
C1'—Sn1—O1—C9	−110.7 (10)	C5'—C6'—C7'—C8'	−64 (3)
C5'—Sn1—O1—C9	111.0 (9)	Sn1—O1—C9—C18	3.2 (12)
C5—Sn1—O2—C20	−136.3 (9)	Sn1—O1—C9—C10	−175.8 (5)
C1—Sn1—O2—C20	120.0 (8)	O1—C9—C10—C11	−180.0 (7)
O1—Sn1—O2—C20	−15.7 (9)	C18—C9—C10—C11	1.0 (11)
N1—Sn1—O2—C20	−8.4 (5)	C9—C10—C11—C12	−1.7 (12)
C1'—Sn1—O2—C20	100.3 (8)	C10—C11—C12—C13	−177.0 (7)
C5'—Sn1—O2—C20	−126.8 (7)	C10—C11—C12—C17	0.2 (11)
C5—Sn1—N1—C19	−86.0 (9)	C11—C12—C13—C14	177.6 (8)
C1—Sn1—N1—C19	97.4 (11)	C17—C12—C13—C14	0.3 (11)
O1—Sn1—N1—C19	3.5 (5)	C12—C13—C14—C15	−0.6 (13)
O2—Sn1—N1—C19	−173.4 (5)	C13—C14—C15—C16	0.4 (14)
C1'—Sn1—N1—C19	105.0 (8)	C14—C15—C16—C17	0.1 (13)
C5'—Sn1—N1—C19	−93.4 (8)	C15—C16—C17—C12	−0.4 (10)
C5—Sn1—N1—N2	95.5 (8)	C15—C16—C17—C18	−179.4 (7)
C1—Sn1—N1—N2	−81.1 (10)	C13—C12—C17—C16	0.1 (9)
O1—Sn1—N1—N2	−175.0 (4)	C11—C12—C17—C16	−177.2 (6)
O2—Sn1—N1—N2	8.1 (3)	C13—C12—C17—C18	179.2 (6)
C1'—Sn1—N1—N2	−73.5 (7)	C11—C12—C17—C18	1.9 (9)
C5'—Sn1—N1—N2	88.1 (8)	O1—C9—C18—C19	2.0 (10)
C19—N1—N2—C20	174.5 (5)	C10—C9—C18—C19	−179.1 (6)
Sn1—N1—N2—C20	−6.8 (5)	O1—C9—C18—C17	−177.8 (6)
C5—Sn1—C1—C2	168 (2)	C10—C9—C18—C17	1.2 (9)
O1—Sn1—C1—C2	72 (2)	C16—C17—C18—C9	176.4 (6)
O2—Sn1—C1—C2	−91 (2)	C12—C17—C18—C9	−2.6 (8)
N1—Sn1—C1—C2	−14 (2)	C16—C17—C18—C19	−3.4 (9)
C1'—Sn1—C1—C2	−33 (2)	C12—C17—C18—C19	177.7 (5)
C5'—Sn1—C1—C2	176.1 (19)	N2—N1—C19—C18	177.9 (5)
Sn1—C1—C2—C3	−175 (2)	Sn1—N1—C19—C18	−0.6 (8)
C1—C2—C3—C4	156 (3)	C9—C18—C19—N1	−3.2 (9)
C1—Sn1—C5—C6	86.3 (19)	C17—C18—C19—N1	176.6 (5)
O1—Sn1—C5—C6	−174.9 (17)	Sn1—O2—C20—N2	8.3 (8)
O2—Sn1—C5—C6	−16.1 (19)	Sn1—O2—C20—C21	−172.3 (4)
N1—Sn1—C5—C6	−91.0 (18)	N1—N2—C20—O2	−1.0 (8)
C1'—Sn1—C5—C6	76 (2)	N1—N2—C20—C21	179.6 (4)
C5'—Sn1—C5—C6	−61 (4)	O2—C20—C21—C26	8.6 (8)
Sn1—C5—C6—C7	−179 (2)	N2—C20—C21—C26	−172.0 (5)
C5—C6—C7—C8	171 (3)	O2—C20—C21—C22	−171.4 (6)
C5—Sn1—C1'—C2'	110 (2)	N2—C20—C21—C22	8.0 (8)
C1—Sn1—C1'—C2'	85 (3)	C26—C21—C22—C23	0.0 (9)
O1—Sn1—C1'—C2'	6 (2)	C20—C21—C22—C23	−179.9 (5)
O2—Sn1—C1'—C2'	−151 (2)	C21—C22—C23—C24	−0.1 (9)
N1—Sn1—C1'—C2'	−80 (2)	C22—C23—C24—O3	−179.5 (5)
C5'—Sn1—C1'—C2'	123 (2)	C22—C23—C24—C25	−0.3 (9)
Sn1—C1'—C2'—C3'	172.6 (15)	O3—C24—C25—C26	179.9 (5)
C1'—C2'—C3'—C4'	111 (3)	C23—C24—C25—C26	0.8 (9)
C5—Sn1—C5'—C6'	64 (4)	C22—C21—C26—C25	0.5 (8)
C1—Sn1—C5'—C6'	29.6 (18)	C20—C21—C26—C25	−179.6 (5)
O1—Sn1—C5'—C6'	132.2 (14)	C24—C25—C26—C21	−0.9 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2ⁱ	0.84	1.99	2.824 (6)	177

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₁₈H₁₂N₂O₃)]
M_r	537.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.6644 (9), 17.2500 (14), 12.9296 (11)
β (°)	106.793 (1)
V (Å³)	2490.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.40 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.678, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	19289, 4391, 2953
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.189, 1.03
No. of reflections	4391
No. of parameters	314
No. of restraints	78
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.19, −1.14

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2ⁱ	0.84	1.99	2.824 (6)	177

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

We thank MOSTI (grant No. 06-01-09-SF0046), Universiti Malaysia Sarawak and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, J.-C., Pan, Q.-X., Yin, H.-D. & Qiao, Y.-L. (2007). Acta Cryst. E63, o2633. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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. Submitted. Google Scholar

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