metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 SnIV 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[Labib, L., Khalil, T. E., Iskander, M. F. & Refaat, L. S. (1996). Polyhedron, 21, 3697-3707.]); Samanta et al. (2007[Samanta, B., Chakraborty, J., Dey, D. K. & Mitra, S. (2007). Struct. Chem. 18, 287-297.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C4H9)2(C18H11BrN2O3)]

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.515, Tmax = 0.621

  • 12053 measured reflections

  • 5740 independent reflections

  • 4886 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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.

Refinement top

One of the two butyl chains is disordered over two positions in all four carbon atoms. The C–C distances were restrained to 1.54±0.01 Å; the anisotropic temperature factors of the carbon atoms were restrained to be nearly isotropic. The disorder refined to a 60 (1):40 (1) ratio.

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent atoms, with Uiso(H) set to 1.2–1.5Ueq(C). The hydroxy H-atom was refined with a distance restraint of 0.84±0.01 Å.

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
[Figure 1] 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
Mr = 616.11F(000) = 616
Triclinic, P1Dx = 1.629 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1626 (2) ÅCell parameters from 5075 reflections
b = 12.2534 (2) Åθ = 2.5–29.6°
c = 12.5583 (2) ŵ = 2.64 mm1
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 tube4886 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.515, Tmax = 0.621k = 1515
12053 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0287P)2 + 0.3063P]
where P = (Fo2 + 2Fc2)/3
5740 reflections(Δ/σ)max = 0.001
342 parametersΔρmax = 0.53 e Å3
47 restraintsΔρmin = 0.59 e Å3
Crystal data top
[Sn(C4H9)2(C18H11BrN2O3)]γ = 65.802 (1)°
Mr = 616.11V = 1256.44 (4) Å3
Triclinic, P1Z = 2
a = 10.1626 (2) ÅMo Kα radiation
b = 12.2534 (2) ŵ = 2.64 mm1
c = 12.5583 (2) ÅT = 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)
Tmin = 0.515, Tmax = 0.621Rint = 0.020
12053 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02547 restraints
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.53 e Å3
5740 reflectionsΔρmin = 0.59 e Å3
342 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.828380 (16)0.685444 (15)0.242560 (14)0.02643 (5)
Br10.66105 (3)1.14077 (3)0.54233 (3)0.04563 (8)
N10.62849 (19)0.86055 (18)0.22108 (16)0.0253 (4)
N20.51208 (19)0.88674 (18)0.15093 (16)0.0269 (4)
O10.91148 (17)0.75767 (16)0.32829 (17)0.0373 (4)
O20.67073 (17)0.70268 (15)0.12755 (14)0.0312 (4)
O30.24653 (18)1.01189 (17)0.04941 (17)0.0377 (4)
H30.316 (2)0.997 (3)0.091 (2)0.043 (8)*
C10.9977 (13)0.6790 (7)0.1322 (11)0.033 (2)0.604 (8)
H1A0.96100.75890.05180.040*0.604 (8)
H1B1.07480.68590.16740.040*0.604 (8)
C21.0651 (6)0.5515 (4)0.1148 (4)0.0393 (14)0.604 (8)
H2A0.98990.54740.07470.047*0.604 (8)
H2B1.14280.55850.06050.047*0.604 (8)
C31.1279 (6)0.4224 (5)0.2312 (5)0.0407 (14)0.604 (8)
H3A1.04890.40690.28110.049*0.604 (8)
H3B1.19400.42990.27740.049*0.604 (8)
C41.2132 (13)0.3006 (7)0.2037 (10)0.053 (3)0.604 (8)
H4A1.24460.21610.27960.079*0.604 (8)
H4B1.29830.31080.16280.079*0.604 (8)
H4C1.15010.29870.15130.079*0.604 (8)
C1'0.9820 (16)0.6826 (9)0.1057 (16)0.027 (3)0.396 (8)
H1C0.93470.69280.03470.032*0.396 (8)
H1D1.00880.75990.07860.032*0.396 (8)
C2'1.1199 (7)0.5504 (6)0.1557 (8)0.037 (2)0.396 (8)
H2C1.19210.55850.09610.044*0.396 (8)
H2D1.16190.53660.23070.044*0.396 (8)
C3'1.0915 (9)0.4283 (7)0.1826 (10)0.047 (2)0.396 (8)
H3C1.05290.43910.10760.056*0.396 (8)
H3D1.01870.41940.24160.056*0.396 (8)
C4'1.2367 (15)0.2992 (9)0.2356 (14)0.045 (3)0.396 (8)
H4D1.22990.22760.22450.068*0.396 (8)
H4E1.25460.26870.32210.068*0.396 (8)
H4F1.31670.32040.19360.068*0.396 (8)
C50.8159 (2)0.5186 (2)0.4004 (2)0.0270 (5)
H5A0.79440.46110.37600.032*
H5B0.91160.46380.44900.032*
C60.7010 (2)0.5593 (2)0.4793 (2)0.0284 (5)
H6A0.72200.61690.50390.034*
H6B0.60490.61320.43150.034*
C70.6958 (3)0.4372 (2)0.5921 (2)0.0334 (5)
H7A0.67580.37920.56730.040*
H7B0.79180.38370.64000.040*
C80.5807 (3)0.4764 (3)0.6711 (2)0.0438 (6)
H8A0.58560.39500.74430.066*
H8B0.48450.52310.62630.066*
H8C0.59780.53650.69350.066*
C90.8505 (2)0.8415 (2)0.3749 (2)0.0300 (5)
C100.9369 (3)0.8446 (2)0.4528 (2)0.0366 (6)
H101.03690.78560.47120.044*
C110.8800 (3)0.9309 (2)0.5027 (2)0.0352 (6)
H110.94020.92970.55650.042*
C120.7347 (3)1.0201 (2)0.4748 (2)0.0323 (5)
C130.6465 (2)1.0216 (2)0.3985 (2)0.0298 (5)
H130.54751.08350.37940.036*
C140.7019 (2)0.9314 (2)0.3481 (2)0.0268 (5)
C150.6026 (2)0.9392 (2)0.2698 (2)0.0265 (5)
H150.50801.00930.25160.032*
C160.5445 (2)0.8009 (2)0.10719 (19)0.0265 (5)
C170.4293 (2)0.8171 (2)0.03210 (19)0.0267 (5)
C180.4605 (2)0.7287 (2)0.01503 (19)0.0265 (5)
H180.55660.66180.00060.032*
C190.3555 (3)0.7338 (2)0.08373 (19)0.0290 (5)
C200.3883 (3)0.6414 (2)0.1309 (2)0.0339 (5)
H200.48470.57570.11880.041*
C210.2825 (3)0.6461 (3)0.1935 (2)0.0408 (6)
H210.30470.58290.22340.049*
C220.1397 (3)0.7457 (3)0.2134 (2)0.0397 (6)
H220.06650.74840.25680.048*
C230.1049 (3)0.8378 (3)0.1720 (2)0.0348 (5)
H230.00860.90470.18790.042*
C240.2118 (2)0.8345 (2)0.1049 (2)0.0292 (5)
C250.1806 (2)0.9263 (2)0.0580 (2)0.0304 (5)
H250.08510.99450.07310.036*
C260.2844 (2)0.9195 (2)0.0086 (2)0.0290 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01985 (8)0.01819 (8)0.03093 (9)0.00410 (6)0.00688 (6)0.00751 (6)
Br10.04928 (17)0.05103 (18)0.05338 (18)0.02710 (14)0.01566 (14)0.03359 (15)
N10.0219 (9)0.0205 (9)0.0239 (9)0.0055 (7)0.0040 (7)0.0059 (7)
N20.0236 (9)0.0225 (9)0.0251 (9)0.0051 (8)0.0031 (8)0.0076 (8)
O10.0220 (8)0.0282 (9)0.0573 (11)0.0044 (7)0.0013 (8)0.0209 (8)
O20.0257 (8)0.0239 (8)0.0356 (9)0.0017 (7)0.0028 (7)0.0144 (7)
O30.0257 (9)0.0317 (9)0.0517 (11)0.0017 (7)0.0001 (8)0.0241 (9)
C10.026 (3)0.035 (3)0.017 (5)0.003 (2)0.003 (2)0.005 (2)
C20.035 (3)0.042 (3)0.028 (2)0.008 (2)0.009 (2)0.015 (2)
C30.033 (3)0.034 (3)0.043 (3)0.009 (2)0.007 (2)0.013 (2)
C40.044 (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)
C50.0246 (11)0.0182 (10)0.0282 (11)0.0058 (9)0.0018 (9)0.0055 (9)
C60.0291 (12)0.0237 (11)0.0279 (12)0.0096 (9)0.0047 (9)0.0098 (9)
C70.0362 (13)0.0282 (12)0.0276 (12)0.0137 (11)0.0043 (10)0.0065 (10)
C80.0462 (16)0.0477 (16)0.0332 (14)0.0236 (13)0.0140 (12)0.0138 (12)
C90.0262 (11)0.0193 (11)0.0358 (13)0.0098 (9)0.0044 (10)0.0058 (9)
C100.0287 (12)0.0214 (12)0.0467 (15)0.0096 (10)0.0042 (11)0.0048 (11)
C110.0391 (14)0.0257 (12)0.0362 (13)0.0196 (11)0.0023 (11)0.0040 (10)
C120.0376 (13)0.0255 (12)0.0331 (13)0.0176 (10)0.0083 (10)0.0101 (10)
C130.0289 (12)0.0236 (11)0.0304 (12)0.0112 (10)0.0088 (10)0.0085 (10)
C140.0257 (11)0.0199 (11)0.0253 (11)0.0087 (9)0.0052 (9)0.0041 (9)
C150.0208 (10)0.0189 (11)0.0286 (11)0.0047 (9)0.0054 (9)0.0058 (9)
C160.0252 (11)0.0211 (11)0.0235 (11)0.0081 (9)0.0075 (9)0.0051 (9)
C170.0272 (11)0.0206 (11)0.0224 (11)0.0081 (9)0.0070 (9)0.0048 (9)
C180.0249 (11)0.0217 (11)0.0214 (11)0.0056 (9)0.0054 (9)0.0050 (9)
C190.0331 (12)0.0248 (11)0.0183 (10)0.0100 (10)0.0064 (9)0.0039 (9)
C200.0360 (13)0.0290 (13)0.0267 (12)0.0074 (10)0.0035 (10)0.0103 (10)
C210.0510 (16)0.0361 (14)0.0293 (13)0.0142 (12)0.0016 (12)0.0130 (11)
C220.0425 (15)0.0428 (15)0.0271 (13)0.0187 (12)0.0000 (11)0.0092 (11)
C230.0318 (13)0.0340 (13)0.0252 (12)0.0129 (11)0.0025 (10)0.0038 (10)
C240.0297 (12)0.0242 (11)0.0217 (11)0.0108 (10)0.0058 (9)0.0022 (9)
C250.0241 (11)0.0237 (11)0.0302 (12)0.0069 (9)0.0066 (9)0.0058 (9)
C260.0290 (12)0.0220 (11)0.0281 (12)0.0087 (9)0.0094 (10)0.0084 (9)
Geometric parameters (Å, º) top
Sn1—O12.0857 (17)C5—H5B0.9900
Sn1—C12.089 (15)C6—C71.525 (3)
Sn1—C52.126 (2)C6—H6A0.9900
Sn1—O22.1531 (16)C6—H6B0.9900
Sn1—C1'2.20 (2)C7—C81.522 (3)
Sn1—N12.1932 (18)C7—H7A0.9900
Br1—C121.895 (2)C7—H7B0.9900
N1—C151.296 (3)C8—H8A0.9800
N1—N21.389 (2)C8—H8B0.9800
N2—C161.316 (3)C8—H8C0.9800
O1—C91.319 (3)C9—C101.405 (3)
O2—C161.295 (3)C9—C141.417 (3)
O3—C261.353 (3)C10—C111.373 (4)
O3—H30.830 (10)C10—H100.9500
C1—C21.538 (7)C11—C121.389 (3)
C1—H1A0.9900C11—H110.9500
C1—H1B0.9900C12—C131.369 (3)
C2—C31.507 (6)C13—C141.415 (3)
C2—H2A0.9900C13—H130.9500
C2—H2B0.9900C14—C151.429 (3)
C3—C41.566 (7)C15—H150.9500
C3—H3A0.9900C16—C171.474 (3)
C3—H3B0.9900C17—C181.377 (3)
C4—H4A0.9800C17—C261.437 (3)
C4—H4B0.9800C18—C191.408 (3)
C4—H4C0.9800C18—H180.9500
C1'—C2'1.538 (9)C19—C201.419 (3)
C1'—H1C0.9900C19—C241.424 (3)
C1'—H1D0.9900C20—C211.367 (3)
C2'—C3'1.516 (8)C20—H200.9500
C2'—H2C0.9900C21—C221.414 (4)
C2'—H2D0.9900C21—H210.9500
C3'—C4'1.563 (9)C22—C231.359 (4)
C3'—H3C0.9900C22—H220.9500
C3'—H3D0.9900C23—C241.422 (3)
C4'—H4D0.9800C23—H230.9500
C4'—H4E0.9800C24—C251.412 (3)
C4'—H4F0.9800C25—C261.369 (3)
C5—C61.525 (3)C25—H250.9500
C5—H5A0.9900
O1—Sn1—C190.6 (3)C7—C6—H6A109.2
O1—Sn1—C597.48 (8)C5—C6—H6A109.2
C1—Sn1—C5126.0 (2)C7—C6—H6B109.2
O1—Sn1—O2153.97 (6)C5—C6—H6B109.2
C1—Sn1—O298.7 (3)H6A—C6—H6B107.9
C5—Sn1—O296.49 (8)C8—C7—C6112.7 (2)
O1—Sn1—C1'98.9 (4)C8—C7—H7A109.0
C1—Sn1—C1'9.2 (6)C6—C7—H7A109.0
C5—Sn1—C1'128.1 (2)C8—C7—H7B109.0
O2—Sn1—C1'89.5 (4)C6—C7—H7B109.0
O1—Sn1—N182.45 (6)H7A—C7—H7B107.8
C1—Sn1—N1128.2 (2)C7—C8—H8A109.5
C5—Sn1—N1105.82 (7)C7—C8—H8B109.5
O2—Sn1—N172.64 (6)H8A—C8—H8B109.5
C1'—Sn1—N1124.9 (2)C7—C8—H8C109.5
C15—N1—N2115.59 (18)H8A—C8—H8C109.5
C15—N1—Sn1128.43 (15)H8B—C8—H8C109.5
N2—N1—Sn1115.90 (13)O1—C9—C10118.8 (2)
C16—N2—N1112.44 (17)O1—C9—C14123.1 (2)
C9—O1—Sn1133.15 (15)C10—C9—C14118.1 (2)
C16—O2—Sn1115.23 (14)C11—C10—C9121.5 (2)
C26—O3—H3110 (2)C11—C10—H10119.3
C2—C1—Sn1114.9 (8)C9—C10—H10119.3
C2—C1—H1A108.5C10—C11—C12120.1 (2)
Sn1—C1—H1A108.5C10—C11—H11119.9
C2—C1—H1B108.5C12—C11—H11119.9
Sn1—C1—H1B108.5C13—C12—C11120.5 (2)
H1A—C1—H1B107.5C13—C12—Br1120.52 (18)
C3—C2—C1113.6 (6)C11—C12—Br1118.98 (18)
C3—C2—H2A108.8C12—C13—C14120.4 (2)
C1—C2—H2A108.8C12—C13—H13119.8
C3—C2—H2B108.8C14—C13—H13119.8
C1—C2—H2B108.8C13—C14—C9119.4 (2)
H2A—C2—H2B107.7C13—C14—C15116.9 (2)
C2—C3—C4110.1 (6)C9—C14—C15123.7 (2)
C2—C3—H3A109.6N1—C15—C14126.7 (2)
C4—C3—H3A109.6N1—C15—H15116.7
C2—C3—H3B109.6C14—C15—H15116.7
C4—C3—H3B109.6O2—C16—N2123.8 (2)
H3A—C3—H3B108.2O2—C16—C17118.5 (2)
C2'—C1'—Sn1111.5 (10)N2—C16—C17117.68 (19)
C2'—C1'—H1C109.3C18—C17—C26118.6 (2)
Sn1—C1'—H1C109.3C18—C17—C16118.82 (19)
C2'—C1'—H1D109.3C26—C17—C16122.6 (2)
Sn1—C1'—H1D109.3C17—C18—C19122.5 (2)
H1C—C1'—H1D108.0C17—C18—H18118.7
C3'—C2'—C1'112.8 (8)C19—C18—H18118.7
C3'—C2'—H2C109.0C18—C19—C20122.1 (2)
C1'—C2'—H2C109.0C18—C19—C24118.3 (2)
C3'—C2'—H2D109.0C20—C19—C24119.6 (2)
C1'—C2'—H2D109.0C21—C20—C19120.5 (2)
H2C—C2'—H2D107.8C21—C20—H20119.7
C2'—C3'—C4'109.0 (7)C19—C20—H20119.7
C2'—C3'—H3C109.9C20—C21—C22119.6 (2)
C4'—C3'—H3C109.9C20—C21—H21120.2
C2'—C3'—H3D109.9C22—C21—H21120.2
C4'—C3'—H3D109.9C23—C22—C21121.5 (2)
H3C—C3'—H3D108.3C23—C22—H22119.3
C3'—C4'—H4D109.5C21—C22—H22119.3
C3'—C4'—H4E109.5C22—C23—C24120.4 (2)
H4D—C4'—H4E109.5C22—C23—H23119.8
C3'—C4'—H4F109.5C24—C23—H23119.8
H4D—C4'—H4F109.5C25—C24—C23122.6 (2)
H4E—C4'—H4F109.5C25—C24—C19119.1 (2)
C6—C5—Sn1113.65 (14)C23—C24—C19118.3 (2)
C6—C5—H5A108.8C26—C25—C24121.6 (2)
Sn1—C5—H5A108.8C26—C25—H25119.2
C6—C5—H5B108.8C24—C25—H25119.2
Sn1—C5—H5B108.8O3—C26—C25118.2 (2)
H5A—C5—H5B107.7O3—C26—C17121.9 (2)
C7—C6—C5112.22 (19)C25—C26—C17119.9 (2)
O1—Sn1—N1—C159.94 (19)C9—C10—C11—C121.4 (4)
C1—Sn1—N1—C1594.8 (4)C10—C11—C12—C130.8 (4)
C5—Sn1—N1—C1585.7 (2)C10—C11—C12—Br1178.50 (18)
O2—Sn1—N1—C15177.7 (2)C11—C12—C13—C140.6 (3)
C1'—Sn1—N1—C15105.6 (5)Br1—C12—C13—C14179.89 (16)
O1—Sn1—N1—N2173.53 (15)C12—C13—C14—C91.4 (3)
C1—Sn1—N1—N288.7 (4)C12—C13—C14—C15179.8 (2)
C5—Sn1—N1—N290.79 (15)O1—C9—C14—C13177.6 (2)
O2—Sn1—N1—N21.18 (13)C10—C9—C14—C130.8 (3)
C1'—Sn1—N1—N277.9 (5)O1—C9—C14—C151.1 (4)
C15—N1—N2—C16178.12 (19)C10—C9—C14—C15179.5 (2)
Sn1—N1—N2—C161.1 (2)N2—N1—C15—C14178.17 (19)
C1—Sn1—O1—C9146.5 (3)Sn1—N1—C15—C141.6 (3)
C5—Sn1—O1—C987.0 (2)C13—C14—C15—N1175.1 (2)
O2—Sn1—O1—C934.9 (3)C9—C14—C15—N16.1 (4)
C1'—Sn1—O1—C9142.4 (3)Sn1—O2—C16—N20.9 (3)
N1—Sn1—O1—C918.1 (2)Sn1—O2—C16—C17178.28 (14)
O1—Sn1—O2—C1618.6 (2)N1—N2—C16—O20.2 (3)
C1—Sn1—O2—C16128.4 (3)N1—N2—C16—C17179.36 (17)
C5—Sn1—O2—C16103.52 (16)O2—C16—C17—C180.9 (3)
C1'—Sn1—O2—C16128.1 (3)N2—C16—C17—C18179.84 (19)
N1—Sn1—O2—C161.07 (14)O2—C16—C17—C26177.4 (2)
O1—Sn1—C1—C2137.0 (6)N2—C16—C17—C261.8 (3)
C5—Sn1—C1—C237.3 (8)C26—C17—C18—C190.9 (3)
O2—Sn1—C1—C267.4 (7)C16—C17—C18—C19177.48 (19)
C1'—Sn1—C1—C269 (3)C17—C18—C19—C20179.3 (2)
N1—Sn1—C1—C2142.1 (5)C17—C18—C19—C240.1 (3)
Sn1—C1—C2—C359.5 (10)C18—C19—C20—C21177.6 (2)
C1—C2—C3—C4171.9 (8)C24—C19—C20—C211.8 (3)
O1—Sn1—C1'—C2'85.7 (8)C19—C20—C21—C221.3 (4)
C1—Sn1—C1'—C2'59 (2)C20—C21—C22—C230.2 (4)
C5—Sn1—C1'—C2'21.2 (11)C21—C22—C23—C241.2 (4)
O2—Sn1—C1'—C2'119.1 (8)C22—C23—C24—C25178.8 (2)
N1—Sn1—C1'—C2'172.7 (6)C22—C23—C24—C190.6 (3)
Sn1—C1'—C2'—C3'67.2 (12)C18—C19—C24—C250.9 (3)
C1'—C2'—C3'—C4'178.6 (11)C20—C19—C24—C25179.7 (2)
O1—Sn1—C5—C668.73 (16)C18—C19—C24—C23178.6 (2)
C1—Sn1—C5—C6165.0 (4)C20—C19—C24—C230.8 (3)
O2—Sn1—C5—C689.24 (16)C23—C24—C25—C26178.5 (2)
C1'—Sn1—C5—C6176.3 (5)C19—C24—C25—C261.0 (3)
N1—Sn1—C5—C615.50 (18)C24—C25—C26—O3179.3 (2)
Sn1—C5—C6—C7179.63 (15)C24—C25—C26—C170.1 (3)
C5—C6—C7—C8179.5 (2)C18—C17—C26—O3178.3 (2)
Sn1—O1—C9—C10164.47 (17)C16—C17—C26—O33.3 (3)
Sn1—O1—C9—C1417.1 (3)C18—C17—C26—C250.8 (3)
O1—C9—C10—C11179.1 (2)C16—C17—C26—C25177.5 (2)
C14—C9—C10—C110.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N20.83 (1)1.88 (2)2.606 (2)146 (3)

Experimental details

Crystal data
Chemical formula[Sn(C4H9)2(C18H11BrN2O3)]
Mr616.11
Crystal system, space groupTriclinic, 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)
V3)1256.44 (4)
Z2
Radiation typeMo Kα
µ (mm1)2.64
Crystal size (mm)0.29 × 0.26 × 0.20
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.515, 0.621
No. of measured, independent and
observed [I > 2σ(I)] reflections
12053, 5740, 4886
Rint0.020
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.060, 1.01
No. of reflections5740
No. of parameters342
No. of restraints47
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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

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

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