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

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

doi:10.1107/S1600536809024477

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m862

doi:10.1107/S1600536809024477

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

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

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

(Received 24 June 2009; accepted 25 June 2009; online 4 July 2009)

The Sn^IV atom in the title compound, [Sn(C₄H₉)₂(C₁₈H₁₁BrN₂O₃)], shows a distorted cis-C₂NO₂Sn trigonal-bipyramidal coordination. One of the butyl chains is disordered over two sites in a 0.60 (1):0.40 (1) ratio.

Related literature

The dianions of similar N′-(2-hydroxybenzylidene)benzohydrazones O,N,O′-chelate to tin in organotin compounds; see: Labib et al. (1996 ); Samanta et al. (2007 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₁₈H₁₁BrN₂O₃)]
M_r = 616.11
Triclinic, $[P \overline 1]$
a = 10.1626 (2) Å
b = 12.2534 (2) Å
c = 12.5583 (2) Å
α = 62.309 (1)°
β = 83.809 (1)°
γ = 65.802 (1)°
V = 1256.44 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 140 K
0.29 × 0.26 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.515, T_max = 0.621
12053 measured reflections
5740 independent reflections
4886 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.060
S = 1.01
5740 reflections
342 parameters
47 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536809024477/xu2544sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024477/xu2544Isup2.hkl

checkCIF report

Related literature top

The dianions of similar N'-(2-hydroxybenzylidene)benzohydrazones O,N,O'-chelate to tin in organotin compounds; see: Labib et al. (1996); Samanta et al. (2007).

Experimental top

The Schiff base (0.39 g, 1 mmol) prepared from the condensation of 5-bromosalicylaldehyde and 3-hydroxy-2-naphthoic hydrazide was heated with dibutyltin oxide (0.25 g, 1 mmol) in ethanol (100 ml) until the oxide dissolved completely. Slow cooling of the filtrate gave the product as yellow crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. Thermal ellipsoid plot (Barbour, 2001) of Sn(C₄H₉)₂(C₁₈H₁₁BrN₂O₃) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one of the two butyl chains is not shown.

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

Crystal data top

[Sn(C₄H₉)₂(C₁₈H₁₁BrN₂O₃)]	Z = 2
M_r = 616.11	F(000) = 616
Triclinic, P1	D_x = 1.629 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1626 (2) Å	Cell parameters from 5075 reflections
b = 12.2534 (2) Å	θ = 2.5–29.6°
c = 12.5583 (2) Å	µ = 2.64 mm⁻¹
α = 62.309 (1)°	T = 140 K
β = 83.809 (1)°	Block, yellow
γ = 65.802 (1)°	0.29 × 0.26 × 0.20 mm
V = 1256.44 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	5740 independent reflections
Radiation source: fine-focus sealed tube	4886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.515, T_max = 0.621	k = −15→15
12053 measured reflections	l = −16→16

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0287P)² + 0.3063P] where P = (F_o² + 2F_c²)/3
5740 reflections	(Δ/σ)_max = 0.001
342 parameters	Δρ_max = 0.53 e Å⁻³
47 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(C₁₈H₁₁BrN₂O₃)]	γ = 65.802 (1)°
M_r = 616.11	V = 1256.44 (4) Å³
Triclinic, P1	Z = 2
a = 10.1626 (2) Å	Mo Kα radiation
b = 12.2534 (2) Å	µ = 2.64 mm⁻¹
c = 12.5583 (2) Å	T = 140 K
α = 62.309 (1)°	0.29 × 0.26 × 0.20 mm
β = 83.809 (1)°

Data collection top

Bruker SMART APEX diffractometer	5740 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4886 reflections with I > 2σ(I)
T_min = 0.515, T_max = 0.621	R_int = 0.020
12053 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	47 restraints
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.53 e Å⁻³
5740 reflections	Δρ_min = −0.59 e Å⁻³
342 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.828380 (16)	0.685444 (15)	0.242560 (14)	0.02643 (5)
Br1	0.66105 (3)	1.14077 (3)	0.54233 (3)	0.04563 (8)
N1	0.62849 (19)	0.86055 (18)	0.22108 (16)	0.0253 (4)
N2	0.51208 (19)	0.88674 (18)	0.15093 (16)	0.0269 (4)
O1	0.91148 (17)	0.75767 (16)	0.32829 (17)	0.0373 (4)
O2	0.67073 (17)	0.70268 (15)	0.12755 (14)	0.0312 (4)
O3	0.24653 (18)	1.01189 (17)	0.04941 (17)	0.0377 (4)
H3	0.316 (2)	0.997 (3)	0.091 (2)	0.043 (8)*
C1	0.9977 (13)	0.6790 (7)	0.1322 (11)	0.033 (2)	0.604 (8)
H1A	0.9610	0.7589	0.0518	0.040*	0.604 (8)
H1B	1.0748	0.6859	0.1674	0.040*	0.604 (8)
C2	1.0651 (6)	0.5515 (4)	0.1148 (4)	0.0393 (14)	0.604 (8)
H2A	0.9899	0.5474	0.0747	0.047*	0.604 (8)
H2B	1.1428	0.5585	0.0605	0.047*	0.604 (8)
C3	1.1279 (6)	0.4224 (5)	0.2312 (5)	0.0407 (14)	0.604 (8)
H3A	1.0489	0.4069	0.2811	0.049*	0.604 (8)
H3B	1.1940	0.4299	0.2774	0.049*	0.604 (8)
C4	1.2132 (13)	0.3006 (7)	0.2037 (10)	0.053 (3)	0.604 (8)
H4A	1.2446	0.2161	0.2796	0.079*	0.604 (8)
H4B	1.2983	0.3108	0.1628	0.079*	0.604 (8)
H4C	1.1501	0.2987	0.1513	0.079*	0.604 (8)
C1'	0.9820 (16)	0.6826 (9)	0.1057 (16)	0.027 (3)	0.396 (8)
H1C	0.9347	0.6928	0.0347	0.032*	0.396 (8)
H1D	1.0088	0.7599	0.0786	0.032*	0.396 (8)
C2'	1.1199 (7)	0.5504 (6)	0.1557 (8)	0.037 (2)	0.396 (8)
H2C	1.1921	0.5585	0.0961	0.044*	0.396 (8)
H2D	1.1619	0.5366	0.2307	0.044*	0.396 (8)
C3'	1.0915 (9)	0.4283 (7)	0.1826 (10)	0.047 (2)	0.396 (8)
H3C	1.0529	0.4391	0.1076	0.056*	0.396 (8)
H3D	1.0187	0.4194	0.2416	0.056*	0.396 (8)
C4'	1.2367 (15)	0.2992 (9)	0.2356 (14)	0.045 (3)	0.396 (8)
H4D	1.2299	0.2276	0.2245	0.068*	0.396 (8)
H4E	1.2546	0.2687	0.3221	0.068*	0.396 (8)
H4F	1.3167	0.3204	0.1936	0.068*	0.396 (8)
C5	0.8159 (2)	0.5186 (2)	0.4004 (2)	0.0270 (5)
H5A	0.7944	0.4611	0.3760	0.032*
H5B	0.9116	0.4638	0.4490	0.032*
C6	0.7010 (2)	0.5593 (2)	0.4793 (2)	0.0284 (5)
H6A	0.7220	0.6169	0.5039	0.034*
H6B	0.6049	0.6132	0.4315	0.034*
C7	0.6958 (3)	0.4372 (2)	0.5921 (2)	0.0334 (5)
H7A	0.6758	0.3792	0.5673	0.040*
H7B	0.7918	0.3837	0.6400	0.040*
C8	0.5807 (3)	0.4764 (3)	0.6711 (2)	0.0438 (6)
H8A	0.5856	0.3950	0.7443	0.066*
H8B	0.4845	0.5231	0.6263	0.066*
H8C	0.5978	0.5365	0.6935	0.066*
C9	0.8505 (2)	0.8415 (2)	0.3749 (2)	0.0300 (5)
C10	0.9369 (3)	0.8446 (2)	0.4528 (2)	0.0366 (6)
H10	1.0369	0.7856	0.4712	0.044*
C11	0.8800 (3)	0.9309 (2)	0.5027 (2)	0.0352 (6)
H11	0.9402	0.9297	0.5565	0.042*
C12	0.7347 (3)	1.0201 (2)	0.4748 (2)	0.0323 (5)
C13	0.6465 (2)	1.0216 (2)	0.3985 (2)	0.0298 (5)
H13	0.5475	1.0835	0.3794	0.036*
C14	0.7019 (2)	0.9314 (2)	0.3481 (2)	0.0268 (5)
C15	0.6026 (2)	0.9392 (2)	0.2698 (2)	0.0265 (5)
H15	0.5080	1.0093	0.2516	0.032*
C16	0.5445 (2)	0.8009 (2)	0.10719 (19)	0.0265 (5)
C17	0.4293 (2)	0.8171 (2)	0.03210 (19)	0.0267 (5)
C18	0.4605 (2)	0.7287 (2)	−0.01503 (19)	0.0265 (5)
H18	0.5566	0.6618	−0.0006	0.032*
C19	0.3555 (3)	0.7338 (2)	−0.08373 (19)	0.0290 (5)
C20	0.3883 (3)	0.6414 (2)	−0.1309 (2)	0.0339 (5)
H20	0.4847	0.5757	−0.1188	0.041*
C21	0.2825 (3)	0.6461 (3)	−0.1935 (2)	0.0408 (6)
H21	0.3047	0.5829	−0.2234	0.049*
C22	0.1397 (3)	0.7457 (3)	−0.2134 (2)	0.0397 (6)
H22	0.0665	0.7484	−0.2568	0.048*
C23	0.1049 (3)	0.8378 (3)	−0.1720 (2)	0.0348 (5)
H23	0.0086	0.9047	−0.1879	0.042*
C24	0.2118 (2)	0.8345 (2)	−0.1049 (2)	0.0292 (5)
C25	0.1806 (2)	0.9263 (2)	−0.0580 (2)	0.0304 (5)
H25	0.0851	0.9945	−0.0731	0.036*
C26	0.2844 (2)	0.9195 (2)	0.0086 (2)	0.0290 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01985 (8)	0.01819 (8)	0.03093 (9)	−0.00410 (6)	0.00688 (6)	−0.00751 (6)
Br1	0.04928 (17)	0.05103 (18)	0.05338 (18)	−0.02710 (14)	0.01566 (14)	−0.03359 (15)
N1	0.0219 (9)	0.0205 (9)	0.0239 (9)	−0.0055 (7)	0.0040 (7)	−0.0059 (7)
N2	0.0236 (9)	0.0225 (9)	0.0251 (9)	−0.0051 (8)	0.0031 (8)	−0.0076 (8)
O1	0.0220 (8)	0.0282 (9)	0.0573 (11)	−0.0044 (7)	0.0013 (8)	−0.0209 (8)
O2	0.0257 (8)	0.0239 (8)	0.0356 (9)	−0.0017 (7)	0.0028 (7)	−0.0144 (7)
O3	0.0257 (9)	0.0317 (9)	0.0517 (11)	−0.0017 (7)	−0.0001 (8)	−0.0241 (9)
C1	0.026 (3)	0.035 (3)	0.017 (5)	−0.003 (2)	0.003 (2)	−0.005 (2)
C2	0.035 (3)	0.042 (3)	0.028 (2)	−0.008 (2)	0.009 (2)	−0.015 (2)
C3	0.033 (3)	0.034 (3)	0.043 (3)	−0.009 (2)	0.007 (2)	−0.013 (2)
C4	0.044 (4)	0.036 (3)	0.062 (6)	−0.007 (3)	0.017 (3)	−0.020 (3)
C1'	0.026 (5)	0.021 (4)	0.019 (7)	−0.007 (3)	0.010 (4)	−0.002 (3)
C2'	0.022 (3)	0.036 (4)	0.041 (4)	−0.008 (3)	0.008 (3)	−0.014 (3)
C3'	0.044 (5)	0.036 (4)	0.057 (6)	−0.016 (3)	0.016 (4)	−0.022 (4)
C4'	0.043 (6)	0.031 (4)	0.050 (6)	−0.011 (4)	0.023 (5)	−0.016 (4)
C5	0.0246 (11)	0.0182 (10)	0.0282 (11)	−0.0058 (9)	0.0018 (9)	−0.0055 (9)
C6	0.0291 (12)	0.0237 (11)	0.0279 (12)	−0.0096 (9)	0.0047 (9)	−0.0098 (9)
C7	0.0362 (13)	0.0282 (12)	0.0276 (12)	−0.0137 (11)	0.0043 (10)	−0.0065 (10)
C8	0.0462 (16)	0.0477 (16)	0.0332 (14)	−0.0236 (13)	0.0140 (12)	−0.0138 (12)
C9	0.0262 (11)	0.0193 (11)	0.0358 (13)	−0.0098 (9)	0.0044 (10)	−0.0058 (9)
C10	0.0287 (12)	0.0214 (12)	0.0467 (15)	−0.0096 (10)	−0.0042 (11)	−0.0048 (11)
C11	0.0391 (14)	0.0257 (12)	0.0362 (13)	−0.0196 (11)	−0.0023 (11)	−0.0040 (10)
C12	0.0376 (13)	0.0255 (12)	0.0331 (13)	−0.0176 (10)	0.0083 (10)	−0.0101 (10)
C13	0.0289 (12)	0.0236 (11)	0.0304 (12)	−0.0112 (10)	0.0088 (10)	−0.0085 (10)
C14	0.0257 (11)	0.0199 (11)	0.0253 (11)	−0.0087 (9)	0.0052 (9)	−0.0041 (9)
C15	0.0208 (10)	0.0189 (11)	0.0286 (11)	−0.0047 (9)	0.0054 (9)	−0.0058 (9)
C16	0.0252 (11)	0.0211 (11)	0.0235 (11)	−0.0081 (9)	0.0075 (9)	−0.0051 (9)
C17	0.0272 (11)	0.0206 (11)	0.0224 (11)	−0.0081 (9)	0.0070 (9)	−0.0048 (9)
C18	0.0249 (11)	0.0217 (11)	0.0214 (11)	−0.0056 (9)	0.0054 (9)	−0.0050 (9)
C19	0.0331 (12)	0.0248 (11)	0.0183 (10)	−0.0100 (10)	0.0064 (9)	−0.0039 (9)
C20	0.0360 (13)	0.0290 (13)	0.0267 (12)	−0.0074 (10)	0.0035 (10)	−0.0103 (10)
C21	0.0510 (16)	0.0361 (14)	0.0293 (13)	−0.0142 (12)	0.0016 (12)	−0.0130 (11)
C22	0.0425 (15)	0.0428 (15)	0.0271 (13)	−0.0187 (12)	0.0000 (11)	−0.0092 (11)
C23	0.0318 (13)	0.0340 (13)	0.0252 (12)	−0.0129 (11)	0.0025 (10)	−0.0038 (10)
C24	0.0297 (12)	0.0242 (11)	0.0217 (11)	−0.0108 (10)	0.0058 (9)	−0.0022 (9)
C25	0.0241 (11)	0.0237 (11)	0.0302 (12)	−0.0069 (9)	0.0066 (9)	−0.0058 (9)
C26	0.0290 (12)	0.0220 (11)	0.0281 (12)	−0.0087 (9)	0.0094 (10)	−0.0084 (9)

Geometric parameters (Å, º) top

Sn1—O1	2.0857 (17)	C5—H5B	0.9900
Sn1—C1	2.089 (15)	C6—C7	1.525 (3)
Sn1—C5	2.126 (2)	C6—H6A	0.9900
Sn1—O2	2.1531 (16)	C6—H6B	0.9900
Sn1—C1'	2.20 (2)	C7—C8	1.522 (3)
Sn1—N1	2.1932 (18)	C7—H7A	0.9900
Br1—C12	1.895 (2)	C7—H7B	0.9900
N1—C15	1.296 (3)	C8—H8A	0.9800
N1—N2	1.389 (2)	C8—H8B	0.9800
N2—C16	1.316 (3)	C8—H8C	0.9800
O1—C9	1.319 (3)	C9—C10	1.405 (3)
O2—C16	1.295 (3)	C9—C14	1.417 (3)
O3—C26	1.353 (3)	C10—C11	1.373 (4)
O3—H3	0.830 (10)	C10—H10	0.9500
C1—C2	1.538 (7)	C11—C12	1.389 (3)
C1—H1A	0.9900	C11—H11	0.9500
C1—H1B	0.9900	C12—C13	1.369 (3)
C2—C3	1.507 (6)	C13—C14	1.415 (3)
C2—H2A	0.9900	C13—H13	0.9500
C2—H2B	0.9900	C14—C15	1.429 (3)
C3—C4	1.566 (7)	C15—H15	0.9500
C3—H3A	0.9900	C16—C17	1.474 (3)
C3—H3B	0.9900	C17—C18	1.377 (3)
C4—H4A	0.9800	C17—C26	1.437 (3)
C4—H4B	0.9800	C18—C19	1.408 (3)
C4—H4C	0.9800	C18—H18	0.9500
C1'—C2'	1.538 (9)	C19—C20	1.419 (3)
C1'—H1C	0.9900	C19—C24	1.424 (3)
C1'—H1D	0.9900	C20—C21	1.367 (3)
C2'—C3'	1.516 (8)	C20—H20	0.9500
C2'—H2C	0.9900	C21—C22	1.414 (4)
C2'—H2D	0.9900	C21—H21	0.9500
C3'—C4'	1.563 (9)	C22—C23	1.359 (4)
C3'—H3C	0.9900	C22—H22	0.9500
C3'—H3D	0.9900	C23—C24	1.422 (3)
C4'—H4D	0.9800	C23—H23	0.9500
C4'—H4E	0.9800	C24—C25	1.412 (3)
C4'—H4F	0.9800	C25—C26	1.369 (3)
C5—C6	1.525 (3)	C25—H25	0.9500
C5—H5A	0.9900

O1—Sn1—C1	90.6 (3)	C7—C6—H6A	109.2
O1—Sn1—C5	97.48 (8)	C5—C6—H6A	109.2
C1—Sn1—C5	126.0 (2)	C7—C6—H6B	109.2
O1—Sn1—O2	153.97 (6)	C5—C6—H6B	109.2
C1—Sn1—O2	98.7 (3)	H6A—C6—H6B	107.9
C5—Sn1—O2	96.49 (8)	C8—C7—C6	112.7 (2)
O1—Sn1—C1'	98.9 (4)	C8—C7—H7A	109.0
C1—Sn1—C1'	9.2 (6)	C6—C7—H7A	109.0
C5—Sn1—C1'	128.1 (2)	C8—C7—H7B	109.0
O2—Sn1—C1'	89.5 (4)	C6—C7—H7B	109.0
O1—Sn1—N1	82.45 (6)	H7A—C7—H7B	107.8
C1—Sn1—N1	128.2 (2)	C7—C8—H8A	109.5
C5—Sn1—N1	105.82 (7)	C7—C8—H8B	109.5
O2—Sn1—N1	72.64 (6)	H8A—C8—H8B	109.5
C1'—Sn1—N1	124.9 (2)	C7—C8—H8C	109.5
C15—N1—N2	115.59 (18)	H8A—C8—H8C	109.5
C15—N1—Sn1	128.43 (15)	H8B—C8—H8C	109.5
N2—N1—Sn1	115.90 (13)	O1—C9—C10	118.8 (2)
C16—N2—N1	112.44 (17)	O1—C9—C14	123.1 (2)
C9—O1—Sn1	133.15 (15)	C10—C9—C14	118.1 (2)
C16—O2—Sn1	115.23 (14)	C11—C10—C9	121.5 (2)
C26—O3—H3	110 (2)	C11—C10—H10	119.3
C2—C1—Sn1	114.9 (8)	C9—C10—H10	119.3
C2—C1—H1A	108.5	C10—C11—C12	120.1 (2)
Sn1—C1—H1A	108.5	C10—C11—H11	119.9
C2—C1—H1B	108.5	C12—C11—H11	119.9
Sn1—C1—H1B	108.5	C13—C12—C11	120.5 (2)
H1A—C1—H1B	107.5	C13—C12—Br1	120.52 (18)
C3—C2—C1	113.6 (6)	C11—C12—Br1	118.98 (18)
C3—C2—H2A	108.8	C12—C13—C14	120.4 (2)
C1—C2—H2A	108.8	C12—C13—H13	119.8
C3—C2—H2B	108.8	C14—C13—H13	119.8
C1—C2—H2B	108.8	C13—C14—C9	119.4 (2)
H2A—C2—H2B	107.7	C13—C14—C15	116.9 (2)
C2—C3—C4	110.1 (6)	C9—C14—C15	123.7 (2)
C2—C3—H3A	109.6	N1—C15—C14	126.7 (2)
C4—C3—H3A	109.6	N1—C15—H15	116.7
C2—C3—H3B	109.6	C14—C15—H15	116.7
C4—C3—H3B	109.6	O2—C16—N2	123.8 (2)
H3A—C3—H3B	108.2	O2—C16—C17	118.5 (2)
C2'—C1'—Sn1	111.5 (10)	N2—C16—C17	117.68 (19)
C2'—C1'—H1C	109.3	C18—C17—C26	118.6 (2)
Sn1—C1'—H1C	109.3	C18—C17—C16	118.82 (19)
C2'—C1'—H1D	109.3	C26—C17—C16	122.6 (2)
Sn1—C1'—H1D	109.3	C17—C18—C19	122.5 (2)
H1C—C1'—H1D	108.0	C17—C18—H18	118.7
C3'—C2'—C1'	112.8 (8)	C19—C18—H18	118.7
C3'—C2'—H2C	109.0	C18—C19—C20	122.1 (2)
C1'—C2'—H2C	109.0	C18—C19—C24	118.3 (2)
C3'—C2'—H2D	109.0	C20—C19—C24	119.6 (2)
C1'—C2'—H2D	109.0	C21—C20—C19	120.5 (2)
H2C—C2'—H2D	107.8	C21—C20—H20	119.7
C2'—C3'—C4'	109.0 (7)	C19—C20—H20	119.7
C2'—C3'—H3C	109.9	C20—C21—C22	119.6 (2)
C4'—C3'—H3C	109.9	C20—C21—H21	120.2
C2'—C3'—H3D	109.9	C22—C21—H21	120.2
C4'—C3'—H3D	109.9	C23—C22—C21	121.5 (2)
H3C—C3'—H3D	108.3	C23—C22—H22	119.3
C3'—C4'—H4D	109.5	C21—C22—H22	119.3
C3'—C4'—H4E	109.5	C22—C23—C24	120.4 (2)
H4D—C4'—H4E	109.5	C22—C23—H23	119.8
C3'—C4'—H4F	109.5	C24—C23—H23	119.8
H4D—C4'—H4F	109.5	C25—C24—C23	122.6 (2)
H4E—C4'—H4F	109.5	C25—C24—C19	119.1 (2)
C6—C5—Sn1	113.65 (14)	C23—C24—C19	118.3 (2)
C6—C5—H5A	108.8	C26—C25—C24	121.6 (2)
Sn1—C5—H5A	108.8	C26—C25—H25	119.2
C6—C5—H5B	108.8	C24—C25—H25	119.2
Sn1—C5—H5B	108.8	O3—C26—C25	118.2 (2)
H5A—C5—H5B	107.7	O3—C26—C17	121.9 (2)
C7—C6—C5	112.22 (19)	C25—C26—C17	119.9 (2)

O1—Sn1—N1—C15	−9.94 (19)	C9—C10—C11—C12	−1.4 (4)
C1—Sn1—N1—C15	−94.8 (4)	C10—C11—C12—C13	0.8 (4)
C5—Sn1—N1—C15	85.7 (2)	C10—C11—C12—Br1	−178.50 (18)
O2—Sn1—N1—C15	177.7 (2)	C11—C12—C13—C14	0.6 (3)
C1'—Sn1—N1—C15	−105.6 (5)	Br1—C12—C13—C14	179.89 (16)
O1—Sn1—N1—N2	173.53 (15)	C12—C13—C14—C9	−1.4 (3)
C1—Sn1—N1—N2	88.7 (4)	C12—C13—C14—C15	179.8 (2)
C5—Sn1—N1—N2	−90.79 (15)	O1—C9—C14—C13	−177.6 (2)
O2—Sn1—N1—N2	1.18 (13)	C10—C9—C14—C13	0.8 (3)
C1'—Sn1—N1—N2	77.9 (5)	O1—C9—C14—C15	1.1 (4)
C15—N1—N2—C16	−178.12 (19)	C10—C9—C14—C15	179.5 (2)
Sn1—N1—N2—C16	−1.1 (2)	N2—N1—C15—C14	178.17 (19)
C1—Sn1—O1—C9	146.5 (3)	Sn1—N1—C15—C14	1.6 (3)
C5—Sn1—O1—C9	−87.0 (2)	C13—C14—C15—N1	−175.1 (2)
O2—Sn1—O1—C9	34.9 (3)	C9—C14—C15—N1	6.1 (4)
C1'—Sn1—O1—C9	142.4 (3)	Sn1—O2—C16—N2	0.9 (3)
N1—Sn1—O1—C9	18.1 (2)	Sn1—O2—C16—C17	−178.28 (14)
O1—Sn1—O2—C16	−18.6 (2)	N1—N2—C16—O2	0.2 (3)
C1—Sn1—O2—C16	−128.4 (3)	N1—N2—C16—C17	179.36 (17)
C5—Sn1—O2—C16	103.52 (16)	O2—C16—C17—C18	−0.9 (3)
C1'—Sn1—O2—C16	−128.1 (3)	N2—C16—C17—C18	179.84 (19)
N1—Sn1—O2—C16	−1.07 (14)	O2—C16—C17—C26	177.4 (2)
O1—Sn1—C1—C2	137.0 (6)	N2—C16—C17—C26	−1.8 (3)
C5—Sn1—C1—C2	37.3 (8)	C26—C17—C18—C19	−0.9 (3)
O2—Sn1—C1—C2	−67.4 (7)	C16—C17—C18—C19	177.48 (19)
C1'—Sn1—C1—C2	−69 (3)	C17—C18—C19—C20	−179.3 (2)
N1—Sn1—C1—C2	−142.1 (5)	C17—C18—C19—C24	0.1 (3)
Sn1—C1—C2—C3	−59.5 (10)	C18—C19—C20—C21	177.6 (2)
C1—C2—C3—C4	−171.9 (8)	C24—C19—C20—C21	−1.8 (3)
O1—Sn1—C1'—C2'	85.7 (8)	C19—C20—C21—C22	1.3 (4)
C1—Sn1—C1'—C2'	59 (2)	C20—C21—C22—C23	0.2 (4)
C5—Sn1—C1'—C2'	−21.2 (11)	C21—C22—C23—C24	−1.2 (4)
O2—Sn1—C1'—C2'	−119.1 (8)	C22—C23—C24—C25	−178.8 (2)
N1—Sn1—C1'—C2'	172.7 (6)	C22—C23—C24—C19	0.6 (3)
Sn1—C1'—C2'—C3'	67.2 (12)	C18—C19—C24—C25	0.9 (3)
C1'—C2'—C3'—C4'	−178.6 (11)	C20—C19—C24—C25	−179.7 (2)
O1—Sn1—C5—C6	68.73 (16)	C18—C19—C24—C23	−178.6 (2)
C1—Sn1—C5—C6	165.0 (4)	C20—C19—C24—C23	0.8 (3)
O2—Sn1—C5—C6	−89.24 (16)	C23—C24—C25—C26	178.5 (2)
C1'—Sn1—C5—C6	176.3 (5)	C19—C24—C25—C26	−1.0 (3)
N1—Sn1—C5—C6	−15.50 (18)	C24—C25—C26—O3	179.3 (2)
Sn1—C5—C6—C7	−179.63 (15)	C24—C25—C26—C17	0.1 (3)
C5—C6—C7—C8	−179.5 (2)	C18—C17—C26—O3	−178.3 (2)
Sn1—O1—C9—C10	164.47 (17)	C16—C17—C26—O3	3.3 (3)
Sn1—O1—C9—C14	−17.1 (3)	C18—C17—C26—C25	0.8 (3)
O1—C9—C10—C11	179.1 (2)	C16—C17—C26—C25	−177.5 (2)
C14—C9—C10—C11	0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.83 (1)	1.88 (2)	2.606 (2)	146 (3)

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₁₈H₁₁BrN₂O₃)]
M_r	616.11
Crystal system, space group	Triclinic, P1
Temperature (K)	140
a, b, c (Å)	10.1626 (2), 12.2534 (2), 12.5583 (2)
α, β, γ (°)	62.309 (1), 83.809 (1), 65.802 (1)
V (Å³)	1256.44 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.64
Crystal size (mm)	0.29 × 0.26 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.515, 0.621
No. of measured, independent and observed [I > 2σ(I)] reflections	12053, 5740, 4886
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.060, 1.01
No. of reflections	5740
No. of parameters	342
No. of restraints	47
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.59

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Labib, L., Khalil, T. E., Iskander, M. F. & Refaat, L. S. (1996). Polyhedron, 21, 3697–3707. CSD CrossRef Web of Science Google Scholar
Samanta, B., Chakraborty, J., Dey, D. K. & Mitra, S. (2007). Struct. Chem. 18, 287–297. Web of Science CSD CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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