[N′-(5-Bromo-2-oxidobenzyl­idene-κO)-3-hydr­oxy-2-naphthohydrazidato-κ2N′,O]dicyclo­hexyl­tin(IV)

Lee, S.M.; Mohd Ali, H.; Lo, K.M.

doi:10.1107/S1600536810001145

metal-organic compounds

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Volume 66| Part 2| February 2010| Page m162

https://doi.org/10.1107/S1600536810001145

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[N′-(5-Bromo-2-oxidobenzylidene-κO)-3-hydroxy-2-naphthohydrazidato-κ²N′,O]dicyclohexyltin(IV)

See Mun Lee,^a Hapipah Mohd Ali ^a and Kong Mun Lo ^a ^*

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

(Received 19 November 2009; accepted 9 January 2010; online 16 January 2010)

The environment at the Sn^IV atom in the title compound, [Sn(C₆H₁₁)₂(C₁₈H₁₁BrN₂O₃)], is distorted trigonal-bipyramidal, with the two cyclohexyl groups and the imino N atom forming the equatorial plane. The axial O—Sn—O angle is 155.97 (9)°. The presence of an intramolecular O—H⋯N hydrogen bond in the Schiff base ligand helps to stabilize the overall structure.

Related literature

For related structures, see Lee et al. (2009a ,b ). For related dianions of similar hydrazone O,N,O′-chelates to tin in organotin compounds, see: Labib et al. (1996 ); Samanta et al. (2007 ).

Experimental

Crystal data

[Sn(C₆H₁₁)₂(C₁₈H₁₁BrN₂O₃)]
M_r = 668.18
Monoclinic, P 2₁ /c
a = 9.2442 (2) Å
b = 9.9949 (2) Å
c = 29.6493 (5) Å
β = 94.874 (1)°
V = 2729.54 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.43 mm⁻¹
T = 140 K
0.33 × 0.30 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.501, T_max = 0.727
20482 measured reflections
4787 independent reflections
4103 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.079
S = 1.09
4787 reflections
335 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.60 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.84	1.86	2.600 (4)	146

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, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810001145/hg2600sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001145/hg2600Isup2.hkl

checkCIF report

Related literature top

For related structures, see Lee et al. (2009a,b). For related dianions of similar hydrazone O,N,O'-chelate to tin in organotin compounds, see: Labib et al. (1996); Samanta et al. (2007).

Experimental top

The Schiff base ligand was prepared by the condensation reaction of 3-hydroxy-2-naphthoyl hydrazide with 5-bromosalicylaldehyde. The title compound was prepared from the equimolar reaction of the prepared Schiff base (0.74 g, 2.0 mmol) and dicyclohexyltin oxide (0.60 g, 2.0 mmol) in toluene. The solution was left for recrystallization for a week during which yellow crystals were obtained.

Structure description top

For related structures, see Lee et al. (2009a,b). For related dianions of similar hydrazone O,N,O'-chelate to tin in organotin compounds, see: Labib et al. (1996); Samanta et al. (2007).

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: pubCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of [N'-(5-bromo-2-oxidobenzylidene-κO)-3-hydroxy-2- naphthohydrazidato-κ²N',O]dicyclohexyltin(IV) showing 50% probability displacement ellipsoids and the atom numbering. Hydrogen atoms are drawn as spheres of arbitrary radius.

[N'-(5-Bromo-2-oxidobenzylidene-κO)-3-hydroxy-2- naphthohydrazidato-κ²N',O]dicyclohexyltin(IV) top

Crystal data top

[Sn(C₆H₁₁)₂(C₁₈H₁₁BrN₂O₃)]	F(000) = 1344
M_r = 668.18	D_x = 1.626 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9975 reflections
a = 9.2442 (2) Å	θ = 2.2–30.4°
b = 9.9949 (2) Å	µ = 2.43 mm⁻¹
c = 29.6493 (5) Å	T = 140 K
β = 94.874 (1)°	Block, yellow
V = 2729.54 (9) Å³	0.33 × 0.30 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4787 independent reflections
Radiation source: fine-focus sealed tube	4103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.501, T_max = 0.727	k = −11→11
20482 measured reflections	l = −35→35

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.030P)² + 5.7701P] where P = (F_o² + 2F_c²)/3
4787 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 1.60 e Å⁻³
1 restraint	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Sn(C₆H₁₁)₂(C₁₈H₁₁BrN₂O₃)]	V = 2729.54 (9) Å³
M_r = 668.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2442 (2) Å	µ = 2.43 mm⁻¹
b = 9.9949 (2) Å	T = 140 K
c = 29.6493 (5) Å	0.33 × 0.30 × 0.14 mm
β = 94.874 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4787 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4103 reflections with I > 2σ(I)
T_min = 0.501, T_max = 0.727	R_int = 0.027
20482 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.079	H-atom parameters constrained
S = 1.09	Δρ_max = 1.60 e Å⁻³
4787 reflections	Δρ_min = −0.49 e Å⁻³
335 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.59441 (3)	0.67684 (3)	0.089632 (8)	0.02876 (9)
Br1	1.11466 (6)	0.10654 (5)	0.162837 (16)	0.04959 (14)
N1	0.7471 (3)	0.6588 (3)	0.14945 (9)	0.0258 (7)
N2	0.7616 (3)	0.7713 (3)	0.17740 (10)	0.0285 (7)
O1	0.6597 (3)	0.4803 (3)	0.07780 (9)	0.0414 (7)
O2	0.5924 (3)	0.8642 (3)	0.12543 (8)	0.0324 (6)
O3	0.8900 (3)	0.9235 (3)	0.23968 (9)	0.0402 (7)
H3	0.8703	0.8519	0.2256	0.060*
C1	0.8416 (4)	0.4343 (4)	0.13884 (12)	0.0268 (8)
C2	0.7606 (4)	0.4016 (4)	0.09761 (12)	0.0318 (9)
C3	0.7907 (5)	0.2795 (4)	0.07729 (14)	0.0426 (11)
H3A	0.7378	0.2555	0.0496	0.051*
C4	0.8943 (5)	0.1934 (4)	0.09617 (14)	0.0414 (10)
H4	0.9133	0.1114	0.0816	0.050*
C5	0.9709 (5)	0.2270 (4)	0.13655 (13)	0.0345 (9)
C6	0.9463 (4)	0.3444 (4)	0.15792 (12)	0.0291 (9)
H6	1.0001	0.3655	0.1858	0.035*
C7	0.8270 (4)	0.5570 (4)	0.16245 (12)	0.0267 (8)
H7	0.8819	0.5652	0.1909	0.032*
C9	0.6882 (4)	0.9979 (4)	0.18743 (11)	0.0252 (8)
C10	0.7946 (4)	1.0198 (4)	0.22456 (11)	0.0286 (8)
C11	0.8030 (4)	1.1420 (4)	0.24509 (13)	0.0343 (9)
H11	0.8773	1.1573	0.2687	0.041*
C12	0.7055 (4)	1.2460 (4)	0.23257 (12)	0.0301 (9)
C13	0.7133 (5)	1.3727 (4)	0.25347 (13)	0.0382 (10)
H13	0.7882	1.3899	0.2767	0.046*
C14	0.6160 (5)	1.4713 (4)	0.24113 (14)	0.0405 (10)
H14	0.6235	1.5561	0.2556	0.049*
C15	0.5039 (5)	1.4469 (4)	0.20675 (14)	0.0415 (10)
H15	0.4342	1.5146	0.1988	0.050*
C16	0.4952 (5)	1.3271 (4)	0.18494 (14)	0.0374 (9)
H16	0.4203	1.3128	0.1614	0.045*
C17	0.5959 (4)	1.2233 (4)	0.19668 (12)	0.0280 (8)
C18	0.5929 (4)	1.0984 (4)	0.17489 (12)	0.0283 (8)
H18	0.5216	1.0832	0.1504	0.034*
C8	0.6791 (4)	0.8710 (4)	0.16197 (11)	0.0251 (8)
C19	0.3711 (4)	0.6283 (4)	0.09615 (13)	0.0349 (9)
H19	0.3689	0.5390	0.1113	0.042*
C20	0.2916 (6)	0.6136 (7)	0.04918 (17)	0.0764 (19)
H20A	0.3390	0.5432	0.0321	0.092*
H20B	0.2973	0.6988	0.0324	0.092*
C21	0.1328 (6)	0.5768 (9)	0.0527 (2)	0.103 (3)
H21A	0.0816	0.5738	0.0220	0.124*
H21B	0.1270	0.4868	0.0663	0.124*
C22	0.0608 (6)	0.6752 (7)	0.0806 (2)	0.085 (2)
H22A	−0.0408	0.6468	0.0832	0.102*
H22B	0.0585	0.7633	0.0653	0.102*
C23	0.1366 (5)	0.6897 (6)	0.12744 (19)	0.0605 (14)
H23A	0.1297	0.6046	0.1442	0.073*
H23B	0.0881	0.7603	0.1441	0.073*
C24	0.2960 (5)	0.7263 (5)	0.12488 (17)	0.0487 (12)
H24A	0.3027	0.8172	0.1119	0.058*
H24B	0.3458	0.7274	0.1558	0.058*
C25	0.6808 (5)	0.7552 (4)	0.03016 (13)	0.0371 (10)
H25	0.7620	0.6946	0.0232	0.044*
C26	0.5679 (6)	0.7490 (6)	−0.01051 (16)	0.0626 (14)
H26A	0.4844	0.8069	−0.0049	0.075*
H26B	0.5320	0.6561	−0.0146	0.075*
C27	0.6336 (8)	0.7955 (7)	−0.05379 (17)	0.084 (2)
H27A	0.7107	0.7323	−0.0611	0.101*
H27B	0.5574	0.7952	−0.0794	0.101*
C28	0.6953 (7)	0.9312 (7)	−0.0481 (2)	0.082 (2)
H28A	0.6161	0.9958	−0.0442	0.098*
H28B	0.7417	0.9564	−0.0758	0.098*
C29	0.8062 (7)	0.9396 (6)	−0.0077 (2)	0.0762 (18)
H29A	0.8397	1.0333	−0.0038	0.091*
H29B	0.8913	0.8838	−0.0133	0.091*
C30	0.7439 (6)	0.8921 (5)	0.03616 (16)	0.0553 (13)
H30A	0.8219	0.8913	0.0612	0.066*
H30B	0.6678	0.9552	0.0443	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03298 (16)	0.02502 (15)	0.02577 (14)	−0.00002 (11)	−0.01213 (10)	−0.00182 (11)
Br1	0.0606 (3)	0.0376 (3)	0.0485 (3)	0.0177 (2)	−0.0080 (2)	0.0070 (2)
N1	0.0310 (17)	0.0238 (17)	0.0212 (15)	−0.0046 (13)	−0.0053 (13)	−0.0007 (13)
N2	0.0329 (18)	0.0245 (17)	0.0263 (16)	−0.0037 (14)	−0.0078 (14)	−0.0043 (13)
O1	0.0531 (19)	0.0277 (15)	0.0383 (15)	0.0068 (13)	−0.0254 (14)	−0.0072 (12)
O2	0.0363 (16)	0.0266 (14)	0.0315 (14)	0.0019 (11)	−0.0141 (12)	−0.0044 (11)
O3	0.0490 (18)	0.0305 (16)	0.0369 (16)	0.0056 (13)	−0.0208 (13)	−0.0051 (12)
C1	0.031 (2)	0.024 (2)	0.0247 (18)	−0.0032 (16)	−0.0020 (16)	0.0026 (15)
C2	0.039 (2)	0.027 (2)	0.027 (2)	−0.0021 (17)	−0.0060 (17)	0.0013 (16)
C3	0.062 (3)	0.029 (2)	0.033 (2)	0.002 (2)	−0.018 (2)	−0.0063 (18)
C4	0.061 (3)	0.024 (2)	0.037 (2)	0.006 (2)	−0.007 (2)	−0.0030 (18)
C5	0.045 (2)	0.026 (2)	0.031 (2)	0.0057 (18)	−0.0014 (18)	0.0083 (17)
C6	0.036 (2)	0.023 (2)	0.0270 (19)	−0.0029 (16)	−0.0042 (16)	0.0045 (15)
C7	0.027 (2)	0.029 (2)	0.0230 (18)	−0.0057 (16)	−0.0052 (15)	0.0025 (15)
C9	0.026 (2)	0.029 (2)	0.0208 (17)	−0.0051 (16)	0.0018 (14)	0.0009 (15)
C10	0.033 (2)	0.031 (2)	0.0209 (18)	0.0002 (17)	−0.0036 (15)	−0.0003 (16)
C11	0.037 (2)	0.037 (2)	0.028 (2)	−0.0048 (18)	−0.0068 (17)	−0.0050 (17)
C12	0.036 (2)	0.030 (2)	0.0255 (19)	−0.0042 (17)	0.0067 (16)	−0.0026 (16)
C13	0.050 (3)	0.036 (2)	0.027 (2)	−0.005 (2)	0.0008 (19)	−0.0052 (18)
C14	0.058 (3)	0.031 (2)	0.035 (2)	0.001 (2)	0.014 (2)	−0.0080 (18)
C15	0.047 (3)	0.037 (2)	0.041 (2)	0.010 (2)	0.009 (2)	−0.002 (2)
C16	0.036 (2)	0.036 (2)	0.039 (2)	0.0025 (19)	0.0006 (18)	0.0014 (19)
C17	0.030 (2)	0.029 (2)	0.0263 (19)	−0.0028 (16)	0.0071 (16)	0.0012 (16)
C18	0.027 (2)	0.032 (2)	0.0254 (19)	−0.0038 (16)	−0.0007 (15)	−0.0006 (16)
C8	0.0224 (19)	0.032 (2)	0.0208 (18)	−0.0048 (16)	−0.0011 (15)	0.0014 (15)
C19	0.034 (2)	0.033 (2)	0.036 (2)	−0.0056 (18)	−0.0085 (18)	0.0028 (18)
C20	0.048 (3)	0.138 (6)	0.041 (3)	−0.035 (3)	−0.008 (2)	−0.012 (3)
C21	0.054 (4)	0.203 (9)	0.050 (3)	−0.063 (5)	−0.011 (3)	−0.016 (4)
C22	0.032 (3)	0.128 (6)	0.092 (5)	−0.011 (3)	−0.012 (3)	0.070 (4)
C23	0.044 (3)	0.056 (3)	0.082 (4)	−0.002 (2)	0.004 (3)	0.006 (3)
C24	0.041 (3)	0.041 (3)	0.064 (3)	−0.007 (2)	0.005 (2)	−0.002 (2)
C25	0.043 (3)	0.039 (2)	0.028 (2)	0.005 (2)	−0.0009 (18)	0.0019 (18)
C26	0.072 (4)	0.072 (4)	0.042 (3)	−0.009 (3)	−0.010 (3)	0.004 (3)
C27	0.100 (5)	0.117 (6)	0.033 (3)	−0.009 (4)	−0.002 (3)	0.006 (3)
C28	0.083 (4)	0.095 (5)	0.069 (4)	0.006 (4)	0.010 (3)	0.042 (4)
C29	0.095 (5)	0.061 (4)	0.076 (4)	−0.017 (3)	0.026 (4)	0.003 (3)
C30	0.066 (3)	0.050 (3)	0.050 (3)	−0.010 (3)	0.002 (2)	−0.003 (2)

Geometric parameters (Å, º) top

Sn1—O1	2.094 (3)	C16—C17	1.418 (6)
Sn1—C25	2.145 (4)	C16—H16	0.9500
Sn1—C19	2.145 (4)	C17—C18	1.405 (5)
Sn1—O2	2.153 (3)	C18—H18	0.9500
Sn1—N1	2.178 (3)	C19—C24	1.506 (6)
Br1—C5	1.910 (4)	C19—C20	1.525 (6)
N1—C7	1.296 (5)	C19—H19	1.0000
N1—N2	1.397 (4)	C20—C21	1.525 (7)
N2—C8	1.313 (5)	C20—H20A	0.9900
O1—C2	1.319 (5)	C20—H20B	0.9900
O2—C8	1.294 (4)	C21—C22	1.480 (10)
O3—C10	1.356 (4)	C21—H21A	0.9900
O3—H3	0.8400	C21—H21B	0.9900
C1—C6	1.404 (5)	C22—C23	1.507 (8)
C1—C2	1.416 (5)	C22—H22A	0.9900
C1—C7	1.425 (5)	C22—H22B	0.9900
C2—C3	1.399 (6)	C23—C24	1.527 (6)
C3—C4	1.371 (6)	C23—H23A	0.9900
C3—H3A	0.9500	C23—H23B	0.9900
C4—C5	1.380 (6)	C24—H24A	0.9900
C4—H4	0.9500	C24—H24B	0.9900
C5—C6	1.362 (5)	C25—C30	1.492 (6)
C6—H6	0.9500	C25—C26	1.527 (6)
C7—H7	0.9500	C25—H25	1.0000
C9—C18	1.367 (5)	C26—C27	1.537 (7)
C9—C10	1.429 (5)	C26—H26A	0.9900
C9—C8	1.475 (5)	C26—H26B	0.9900
C10—C11	1.364 (5)	C27—C28	1.476 (9)
C11—C12	1.404 (6)	C27—H27A	0.9900
C11—H11	0.9500	C27—H27B	0.9900
C12—C13	1.409 (6)	C28—C29	1.513 (8)
C12—C17	1.424 (5)	C28—H28A	0.9900
C13—C14	1.363 (6)	C28—H28B	0.9900
C13—H13	0.9500	C29—C30	1.540 (7)
C14—C15	1.411 (6)	C29—H29A	0.9900
C14—H14	0.9500	C29—H29B	0.9900
C15—C16	1.360 (6)	C30—H30A	0.9900
C15—H15	0.9500	C30—H30B	0.9900

O1—Sn1—C25	94.14 (15)	C24—C19—Sn1	113.4 (3)
O1—Sn1—C19	95.51 (14)	C20—C19—Sn1	109.4 (3)
C25—Sn1—C19	125.81 (15)	C24—C19—H19	107.4
O1—Sn1—O2	155.97 (9)	C20—C19—H19	107.4
C25—Sn1—O2	96.14 (14)	Sn1—C19—H19	107.4
C19—Sn1—O2	95.96 (13)	C19—C20—C21	110.7 (4)
O1—Sn1—N1	83.25 (10)	C19—C20—H20A	109.5
C25—Sn1—N1	116.02 (14)	C21—C20—H20A	109.5
C19—Sn1—N1	118.03 (13)	C19—C20—H20B	109.5
O2—Sn1—N1	72.71 (10)	C21—C20—H20B	109.5
C7—N1—N2	115.6 (3)	H20A—C20—H20B	108.1
C7—N1—Sn1	128.4 (2)	C22—C21—C20	111.0 (6)
N2—N1—Sn1	116.1 (2)	C22—C21—H21A	109.4
C8—N2—N1	112.4 (3)	C20—C21—H21A	109.4
C2—O1—Sn1	133.4 (2)	C22—C21—H21B	109.4
C8—O2—Sn1	115.3 (2)	C20—C21—H21B	109.4
C10—O3—H3	109.5	H21A—C21—H21B	108.0
C6—C1—C2	119.7 (3)	C21—C22—C23	112.6 (5)
C6—C1—C7	116.4 (3)	C21—C22—H22A	109.1
C2—C1—C7	123.9 (3)	C23—C22—H22A	109.1
O1—C2—C3	119.1 (3)	C21—C22—H22B	109.1
O1—C2—C1	123.3 (3)	C23—C22—H22B	109.1
C3—C2—C1	117.6 (3)	H22A—C22—H22B	107.8
C4—C3—C2	121.9 (4)	C22—C23—C24	110.6 (4)
C4—C3—H3A	119.0	C22—C23—H23A	109.5
C2—C3—H3A	119.0	C24—C23—H23A	109.5
C3—C4—C5	119.4 (4)	C22—C23—H23B	109.5
C3—C4—H4	120.3	C24—C23—H23B	109.5
C5—C4—H4	120.3	H23A—C23—H23B	108.1
C6—C5—C4	121.3 (4)	C19—C24—C23	111.5 (4)
C6—C5—Br1	119.4 (3)	C19—C24—H24A	109.3
C4—C5—Br1	119.3 (3)	C23—C24—H24A	109.3
C5—C6—C1	120.0 (3)	C19—C24—H24B	109.3
C5—C6—H6	120.0	C23—C24—H24B	109.3
C1—C6—H6	120.0	H24A—C24—H24B	108.0
N1—C7—C1	127.2 (3)	C30—C25—C26	111.4 (4)
N1—C7—H7	116.4	C30—C25—Sn1	114.0 (3)
C1—C7—H7	116.4	C26—C25—Sn1	110.9 (3)
C18—C9—C10	118.8 (3)	C30—C25—H25	106.7
C18—C9—C8	119.1 (3)	C26—C25—H25	106.7
C10—C9—C8	122.1 (3)	Sn1—C25—H25	106.7
O3—C10—C11	118.5 (3)	C25—C26—C27	110.8 (4)
O3—C10—C9	122.1 (3)	C25—C26—H26A	109.5
C11—C10—C9	119.3 (3)	C27—C26—H26A	109.5
C10—C11—C12	122.3 (3)	C25—C26—H26B	109.5
C10—C11—H11	118.9	C27—C26—H26B	109.5
C12—C11—H11	118.9	H26A—C26—H26B	108.1
C11—C12—C13	122.8 (4)	C28—C27—C26	111.0 (5)
C11—C12—C17	118.6 (3)	C28—C27—H27A	109.4
C13—C12—C17	118.6 (4)	C26—C27—H27A	109.4
C14—C13—C12	121.6 (4)	C28—C27—H27B	109.4
C14—C13—H13	119.2	C26—C27—H27B	109.4
C12—C13—H13	119.2	H27A—C27—H27B	108.0
C13—C14—C15	119.8 (4)	C27—C28—C29	111.8 (5)
C13—C14—H14	120.1	C27—C28—H28A	109.3
C15—C14—H14	120.1	C29—C28—H28A	109.3
C16—C15—C14	120.4 (4)	C27—C28—H28B	109.3
C16—C15—H15	119.8	C29—C28—H28B	109.3
C14—C15—H15	119.8	H28A—C28—H28B	107.9
C15—C16—C17	121.1 (4)	C28—C29—C30	112.0 (5)
C15—C16—H16	119.5	C28—C29—H29A	109.2
C17—C16—H16	119.5	C30—C29—H29A	109.2
C18—C17—C16	123.4 (4)	C28—C29—H29B	109.2
C18—C17—C12	118.1 (3)	C30—C29—H29B	109.2
C16—C17—C12	118.5 (4)	H29A—C29—H29B	107.9
C9—C18—C17	122.8 (3)	C25—C30—C29	110.6 (4)
C9—C18—H18	118.6	C25—C30—H30A	109.5
C17—C18—H18	118.6	C29—C30—H30A	109.5
O2—C8—N2	123.5 (3)	C25—C30—H30B	109.5
O2—C8—C9	118.6 (3)	C29—C30—H30B	109.5
N2—C8—C9	117.9 (3)	H30A—C30—H30B	108.1
C24—C19—C20	111.7 (4)

O1—Sn1—N1—C7	0.0 (3)	C15—C16—C17—C18	−179.2 (4)
C25—Sn1—N1—C7	−91.3 (3)	C15—C16—C17—C12	1.2 (6)
C19—Sn1—N1—C7	92.7 (3)	C11—C12—C17—C18	−1.4 (5)
O2—Sn1—N1—C7	−179.8 (3)	C13—C12—C17—C18	177.5 (4)
O1—Sn1—N1—N2	179.7 (3)	C11—C12—C17—C16	178.3 (4)
C25—Sn1—N1—N2	88.4 (3)	C13—C12—C17—C16	−2.9 (5)
C19—Sn1—N1—N2	−87.6 (3)	C10—C9—C18—C17	0.7 (6)
O2—Sn1—N1—N2	0.0 (2)	C8—C9—C18—C17	−178.6 (3)
C7—N1—N2—C8	179.2 (3)	C16—C17—C18—C9	−178.1 (4)
Sn1—N1—N2—C8	−0.6 (4)	C12—C17—C18—C9	1.5 (6)
C25—Sn1—O1—C2	109.0 (4)	Sn1—O2—C8—N2	−1.3 (5)
C19—Sn1—O1—C2	−124.4 (4)	Sn1—O2—C8—C9	177.7 (2)
O2—Sn1—O1—C2	−6.2 (6)	N1—N2—C8—O2	1.3 (5)
N1—Sn1—O1—C2	−6.8 (4)	N1—N2—C8—C9	−177.7 (3)
O1—Sn1—O2—C8	0.1 (4)	C18—C9—C8—O2	7.8 (5)
C25—Sn1—O2—C8	−114.7 (3)	C10—C9—C8—O2	−171.5 (3)
C19—Sn1—O2—C8	118.2 (3)	C18—C9—C8—N2	−173.2 (3)
N1—Sn1—O2—C8	0.7 (2)	C10—C9—C8—N2	7.5 (5)
Sn1—O1—C2—C3	−171.0 (3)	O1—Sn1—C19—C24	153.9 (3)
Sn1—O1—C2—C1	8.8 (6)	C25—Sn1—C19—C24	−106.9 (3)
C6—C1—C2—O1	179.4 (4)	O2—Sn1—C19—C24	−4.9 (3)
C7—C1—C2—O1	−2.4 (6)	N1—Sn1—C19—C24	68.6 (3)
C6—C1—C2—C3	−0.7 (6)	O1—Sn1—C19—C20	−80.7 (4)
C7—C1—C2—C3	177.5 (4)	C25—Sn1—C19—C20	18.4 (4)
O1—C2—C3—C4	179.9 (4)	O2—Sn1—C19—C20	120.4 (4)
C1—C2—C3—C4	0.1 (7)	N1—Sn1—C19—C20	−166.0 (4)
C2—C3—C4—C5	0.5 (7)	C24—C19—C20—C21	−54.5 (7)
C3—C4—C5—C6	−0.4 (7)	Sn1—C19—C20—C21	179.1 (5)
C3—C4—C5—Br1	179.8 (4)	C19—C20—C21—C22	55.3 (8)
C4—C5—C6—C1	−0.2 (6)	C20—C21—C22—C23	−56.7 (7)
Br1—C5—C6—C1	179.6 (3)	C21—C22—C23—C24	55.8 (7)
C2—C1—C6—C5	0.8 (6)	C20—C19—C24—C23	54.3 (5)
C7—C1—C6—C5	−177.5 (4)	Sn1—C19—C24—C23	178.4 (3)
N2—N1—C7—C1	−175.0 (3)	C22—C23—C24—C19	−54.0 (6)
Sn1—N1—C7—C1	4.7 (6)	O1—Sn1—C25—C30	−143.8 (3)
C6—C1—C7—N1	173.8 (4)	C19—Sn1—C25—C30	116.3 (3)
C2—C1—C7—N1	−4.4 (6)	O2—Sn1—C25—C30	14.4 (3)
C18—C9—C10—O3	178.2 (4)	N1—Sn1—C25—C30	−59.3 (4)
C8—C9—C10—O3	−2.5 (6)	O1—Sn1—C25—C26	89.5 (3)
C18—C9—C10—C11	−3.1 (6)	C19—Sn1—C25—C26	−10.4 (4)
C8—C9—C10—C11	176.2 (4)	O2—Sn1—C25—C26	−112.3 (3)
O3—C10—C11—C12	−177.9 (4)	N1—Sn1—C25—C26	174.0 (3)
C9—C10—C11—C12	3.4 (6)	C30—C25—C26—C27	56.1 (6)
C10—C11—C12—C13	−179.9 (4)	Sn1—C25—C26—C27	−175.8 (4)
C10—C11—C12—C17	−1.1 (6)	C25—C26—C27—C28	−56.2 (7)
C11—C12—C13—C14	−179.0 (4)	C26—C27—C28—C29	55.7 (8)
C17—C12—C13—C14	2.2 (6)	C27—C28—C29—C30	−54.9 (8)
C12—C13—C14—C15	0.2 (6)	C26—C25—C30—C29	−54.8 (6)
C13—C14—C15—C16	−2.0 (6)	Sn1—C25—C30—C29	178.8 (4)
C14—C15—C16—C17	1.3 (6)	C28—C29—C30—C25	54.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.84	1.86	2.600 (4)	146

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₁₁)₂(C₁₈H₁₁BrN₂O₃)]
M_r	668.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	140
a, b, c (Å)	9.2442 (2), 9.9949 (2), 29.6493 (5)
β (°)	94.874 (1)
V (Å³)	2729.54 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.43
Crystal size (mm)	0.33 × 0.30 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.501, 0.727
No. of measured, independent and observed [I > 2σ(I)] reflections	20482, 4787, 4103
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.079, 1.09
No. of reflections	4787
No. of parameters	335
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.60, −0.49

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.84	1.86	2.600 (4)	146.1

Acknowledgements

We thank the University of Malaya (grant Nos. PS320/2008 C and RG020/09AFR) for supporting this study.

References

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