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

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ISSN: 2056-9890

{N′-[1-(5-Bromo-2-oxido­phenyl-κO)ethyl­­idene]-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 26 June 2009; online 4 July 2009)

The SnIV atom in the title compound, [Sn(C4H9)2(C19H13BrN2O3)], shows a distorted cis-C2NO2Sn trigonal-bipyramidal coordination. Both butyl chains and the naphth­yl­oxy portion are disordered over two sets of sites of equal occupancy.

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(C19H13BrN2O3)]

  • Mr = 630.14

  • Monoclinic, P 21 /c

  • a = 14.2649 (2) Å

  • b = 7.2249 (1) Å

  • c = 24.9527 (3) Å

  • β = 95.483 (1)°

  • V = 2559.92 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.59 mm−1

  • T = 140 K

  • 0.40 × 0.30 × 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 = 0.424, Tmax = 0.625

  • 23522 measured reflections

  • 5885 independent reflections

  • 5168 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.114

  • S = 1.26

  • 5885 reflections

  • 318 parameters

  • 160 restraints

  • H-atom parameters constrained

  • Δρmax = 1.36 e Å−3

  • Δρmin = −1.07 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 (0.4 g, 1 mmol) from the condensation reaction of 5-bromo-2'-hydroxyacetophenone and 3-hydroxy-2-naphthoic hydrazide and dibutyltin oxide (0.25 g, 1 mmol) were dissolved heated in ethanol (100 ml) until the oxide dissolved completely over an hour. Slow cooling of the filtrate gave the product as yellow crystals.

Refinement top

Both butyl chains are disordered over two positions. One chain is disodered in all four carbon atoms whereas the other is disordered in only the β, γ and δ atoms only. As the occupancy refined to nearly 50:50, this was fixed as exactly 50:50. The C–C distance was tightly restrained to 1.500±0.005 Å and the C···C distance to 2.35±0.01 Å.

The hydroxynaphthyl portion is alo disordered over two positions. The occupancy was also set as 50:50. The naphthyl fused-ring was refined as a rigid ring of 1.39 Å sides. The C17–C19 and C17–C19' distances were restrained to within 0.01 Å of each other, as were the O3–C20 and O3'–C20' distances.

For the chains and fused-ring, the temperature factors of the primed atoms were restrained to those of the unprimed ones; the anisotropic temperature factors were restrained to be nearly isotropic.

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5Ueq(C). The hydroxy H-atom was similarly treated.

The final difference map had a peak near Sn1 and a hole near Br1.

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(C19H13BrN2O3) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. One of the disordered components is not shown.
{N'-[1-(5-Bromo-2-oxidophenyl-κO)ethylidene]-3- hydroxy-2-naphthohydrazidato-κ2N',O}dibutyltin(IV) top
Crystal data top
[Sn(C4H9)2(C19H13BrN2O3)]F(000) = 1264
Mr = 630.14Dx = 1.635 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9057 reflections
a = 14.2649 (2) Åθ = 2.7–30.2°
b = 7.2249 (1) ŵ = 2.59 mm1
c = 24.9527 (3) ÅT = 140 K
β = 95.483 (1)°Block, yellow
V = 2559.92 (6) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
5885 independent reflections
Radiation source: fine-focus sealed tube5168 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1818
Tmin = 0.424, Tmax = 0.625k = 99
23522 measured reflectionsl = 3232
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.26 w = 1/[σ2(Fo2) + (0.05P)2 + 5P]
where P = (Fo2 + 2Fc2)/3
5885 reflections(Δ/σ)max = 0.001
318 parametersΔρmax = 1.36 e Å3
160 restraintsΔρmin = 1.07 e Å3
Crystal data top
[Sn(C4H9)2(C19H13BrN2O3)]V = 2559.92 (6) Å3
Mr = 630.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.2649 (2) ŵ = 2.59 mm1
b = 7.2249 (1) ÅT = 140 K
c = 24.9527 (3) Å0.40 × 0.30 × 0.20 mm
β = 95.483 (1)°
Data collection top
Bruker SMART APEX
diffractometer
5885 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5168 reflections with I > 2σ(I)
Tmin = 0.424, Tmax = 0.625Rint = 0.031
23522 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043160 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.26Δρmax = 1.36 e Å3
5885 reflectionsΔρmin = 1.07 e Å3
318 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.72540 (2)0.55576 (4)0.662024 (11)0.02024 (10)
Br11.03334 (3)0.81137 (9)0.906936 (19)0.03699 (15)
O10.8347 (2)0.4432 (4)0.71201 (12)0.0240 (6)
O20.5866 (2)0.6711 (4)0.64649 (12)0.0292 (7)
O30.4054 (8)0.5807 (12)0.7760 (3)0.0225 (14)0.50
H30.46400.57530.78380.034*0.50
O3'0.4054 (8)0.6330 (12)0.7628 (3)0.0225 (14)0.50
H3'0.46340.62630.77230.034*0.50
N10.6717 (2)0.6122 (5)0.73982 (13)0.0176 (7)
N20.5737 (2)0.6253 (5)0.73690 (15)0.0221 (7)
C10.8061 (10)0.775 (2)0.6303 (3)0.025 (2)0.50
H1A0.79810.88770.65180.029*0.50
H1B0.87350.74000.63540.029*0.50
C20.7814 (7)0.8201 (10)0.5719 (3)0.0256 (13)0.50
H2A0.71250.83830.56490.031*0.50
H2B0.81300.93630.56280.031*0.50
C30.8119 (7)0.6666 (11)0.5379 (3)0.0257 (16)0.50
H3A0.77590.55310.54470.031*0.50
H3B0.87960.64060.54750.031*0.50
C40.7958 (8)0.7182 (15)0.4797 (3)0.0352 (17)0.50
H4A0.79130.60560.45770.053*0.50
H4B0.84840.79410.46980.053*0.50
H4C0.73700.78860.47340.053*0.50
C1'0.7823 (9)0.813 (2)0.6364 (3)0.025 (2)0.50
H1'A0.72950.89950.62700.029*0.50
H1'B0.82210.86710.66710.029*0.50
C2'0.8397 (6)0.7984 (12)0.5893 (3)0.0256 (13)0.50
H2'A0.86450.92200.58100.031*0.50
H2'B0.89390.71500.59850.031*0.50
C3'0.7811 (5)0.7253 (14)0.5414 (3)0.0257 (16)0.50
H3'A0.72840.81100.53100.031*0.50
H3'B0.75460.60330.54980.031*0.50
C4'0.8425 (7)0.7066 (15)0.4961 (3)0.0352 (17)0.50
H4'A0.80380.67050.46320.053*0.50
H4'B0.89050.61180.50520.053*0.50
H4'C0.87320.82530.49030.053*0.50
C50.6858 (3)0.2933 (7)0.62678 (19)0.0312 (11)
H5A0.73580.25110.60470.037*0.50
H5B0.68110.20160.65590.037*0.50
H5C0.72340.27640.59580.037*0.50
H5D0.70850.19970.65390.037*0.50
C60.5922 (5)0.2992 (10)0.5915 (3)0.0248 (16)0.50
H6A0.54260.34980.61250.030*0.50
H6B0.59800.38220.56040.030*0.50
C70.5645 (5)0.1108 (10)0.5717 (3)0.0260 (13)0.50
H7A0.56080.02660.60270.031*0.50
H7B0.61280.06200.54940.031*0.50
C80.4706 (6)0.1169 (14)0.5387 (4)0.0367 (16)0.50
H8A0.45330.00800.52600.055*0.50
H8B0.47470.19870.50770.055*0.50
H8C0.42280.16390.56090.055*0.50
C6'0.5857 (4)0.2476 (13)0.6092 (3)0.0248 (16)0.50
H6'A0.57640.11190.60740.030*0.50
H6'B0.54340.30020.63440.030*0.50
C7'0.5664 (5)0.3320 (12)0.5547 (3)0.0260 (13)0.50
H7'A0.60730.27580.52930.031*0.50
H7'B0.57880.46680.55650.031*0.50
C8'0.4646 (5)0.2961 (15)0.5365 (4)0.0367 (16)0.50
H8'A0.44740.36230.50270.055*0.50
H8'B0.42530.33950.56400.055*0.50
H8'C0.45490.16300.53070.055*0.50
C90.8749 (3)0.5319 (5)0.75490 (17)0.0188 (8)
C100.9737 (3)0.5253 (6)0.76486 (19)0.0226 (9)
H101.00920.46190.74020.027*
C111.0200 (3)0.6084 (6)0.80931 (18)0.0214 (8)
H111.08680.60380.81520.026*
C120.9682 (3)0.6989 (6)0.84552 (16)0.0212 (8)
C130.8721 (3)0.7089 (6)0.83758 (16)0.0195 (8)
H130.83840.77330.86290.023*
C140.8220 (3)0.6247 (5)0.79235 (15)0.0163 (7)
C150.7191 (3)0.6337 (5)0.78681 (15)0.0166 (7)
C160.6671 (3)0.6700 (6)0.83560 (16)0.0205 (8)
H16A0.60650.60520.83170.031*
H16B0.65630.80330.83890.031*
H16C0.70480.62520.86790.031*
C170.5374 (3)0.6540 (6)0.68713 (18)0.0249 (9)
C180.3848 (2)0.7007 (9)0.63169 (18)0.0194 (15)0.50
H180.42330.72340.60340.023*0.50
C190.4258 (2)0.6540 (9)0.6827 (2)0.0189 (14)0.50
C200.3694 (3)0.6209 (9)0.72411 (17)0.0185 (15)0.50
C210.2721 (3)0.6345 (7)0.71459 (14)0.0192 (14)0.50
H210.23350.61190.74290.023*0.50
C220.2310 (2)0.6813 (5)0.66361 (14)0.0182 (14)0.50
C230.2874 (2)0.7144 (6)0.62216 (13)0.0174 (15)0.50
C240.2464 (3)0.7612 (8)0.57118 (14)0.0258 (15)0.50
H240.28490.78380.54290.031*0.50
C250.1490 (3)0.7748 (8)0.56165 (17)0.0278 (15)0.50
H250.12100.80680.52680.033*0.50
C260.0927 (2)0.7417 (8)0.6031 (2)0.0266 (15)0.50
H260.02610.75110.59660.032*0.50
C270.1337 (2)0.6950 (7)0.65408 (19)0.0240 (13)0.50
H270.09520.67240.68240.029*0.50
C18'0.4052 (2)0.7136 (9)0.61716 (18)0.0194 (15)0.50
H18'0.44870.72510.59080.023*0.50
C19'0.4376 (2)0.6775 (10)0.6704 (2)0.0189 (14)0.50
C20'0.3740 (3)0.6606 (8)0.70904 (16)0.0185 (15)0.50
C21'0.2780 (3)0.6799 (7)0.69436 (14)0.0192 (14)0.50
H21'0.23460.66840.72070.023*0.50
C22'0.2456 (2)0.7160 (5)0.64107 (14)0.0182 (14)0.50
C23'0.3092 (2)0.7328 (6)0.60247 (14)0.0174 (15)0.50
C24'0.2768 (3)0.7690 (8)0.54918 (14)0.0258 (15)0.50
H24'0.32030.78050.52280.031*0.50
C25'0.1809 (3)0.7882 (8)0.53450 (16)0.0278 (15)0.50
H25'0.15870.81290.49810.033*0.50
C26'0.1173 (3)0.7714 (8)0.5731 (2)0.0266 (15)0.50
H26B0.05170.78460.56310.032*0.50
C27'0.1497 (2)0.7353 (7)0.62638 (19)0.0240 (13)0.50
H27'0.10620.72370.65280.029*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02501 (16)0.02065 (15)0.01516 (15)0.00916 (11)0.00247 (10)0.00324 (10)
Br10.0226 (2)0.0629 (4)0.0237 (2)0.0061 (2)0.00660 (17)0.0052 (2)
O10.0206 (15)0.0243 (15)0.0275 (16)0.0007 (12)0.0045 (12)0.0100 (12)
O20.0418 (19)0.0202 (15)0.0231 (16)0.0017 (14)0.0097 (14)0.0005 (12)
O30.0197 (16)0.028 (4)0.020 (3)0.001 (3)0.003 (2)0.004 (2)
O3'0.0197 (16)0.028 (4)0.020 (3)0.001 (3)0.003 (2)0.004 (2)
N10.0179 (16)0.0150 (15)0.0195 (16)0.0031 (13)0.0009 (13)0.0006 (13)
N20.0181 (17)0.0212 (17)0.0256 (18)0.0063 (14)0.0049 (14)0.0086 (14)
C10.021 (7)0.021 (7)0.033 (3)0.007 (4)0.005 (3)0.002 (3)
C20.029 (3)0.022 (2)0.027 (3)0.002 (2)0.006 (2)0.003 (2)
C30.022 (3)0.027 (3)0.028 (2)0.002 (2)0.002 (2)0.002 (2)
C40.038 (3)0.035 (3)0.033 (3)0.003 (3)0.007 (3)0.003 (2)
C1'0.021 (7)0.021 (7)0.033 (3)0.007 (4)0.005 (3)0.002 (3)
C2'0.029 (3)0.022 (2)0.027 (3)0.002 (2)0.006 (2)0.003 (2)
C3'0.022 (3)0.027 (3)0.028 (2)0.002 (2)0.002 (2)0.002 (2)
C4'0.038 (3)0.035 (3)0.033 (3)0.003 (3)0.007 (3)0.003 (2)
C50.026 (2)0.032 (2)0.038 (3)0.0160 (19)0.0135 (19)0.020 (2)
C60.023 (2)0.022 (3)0.031 (3)0.013 (2)0.012 (2)0.004 (2)
C70.027 (3)0.026 (2)0.024 (2)0.002 (2)0.001 (2)0.003 (2)
C80.036 (3)0.038 (3)0.036 (3)0.001 (2)0.002 (2)0.004 (2)
C6'0.023 (2)0.022 (3)0.031 (3)0.013 (2)0.012 (2)0.004 (2)
C7'0.027 (3)0.026 (2)0.024 (2)0.002 (2)0.001 (2)0.003 (2)
C8'0.036 (3)0.038 (3)0.036 (3)0.001 (2)0.002 (2)0.004 (2)
C90.021 (2)0.0127 (18)0.023 (2)0.0001 (15)0.0037 (15)0.0008 (15)
C100.018 (2)0.0156 (19)0.035 (2)0.0025 (15)0.0067 (17)0.0023 (16)
C110.0153 (19)0.0156 (18)0.033 (2)0.0008 (15)0.0012 (16)0.0076 (16)
C120.023 (2)0.0216 (19)0.0184 (19)0.0025 (16)0.0033 (15)0.0051 (16)
C130.023 (2)0.0181 (19)0.0175 (19)0.0013 (15)0.0009 (15)0.0026 (15)
C140.0187 (19)0.0130 (17)0.0169 (18)0.0000 (14)0.0003 (14)0.0015 (14)
C150.021 (2)0.0110 (17)0.0177 (18)0.0021 (14)0.0021 (15)0.0013 (14)
C160.0183 (19)0.022 (2)0.022 (2)0.0003 (16)0.0039 (15)0.0018 (16)
C170.031 (2)0.0129 (19)0.029 (2)0.0060 (16)0.0079 (18)0.0073 (16)
C180.022 (3)0.017 (2)0.019 (3)0.004 (2)0.002 (3)0.002 (2)
C190.022 (2)0.012 (2)0.022 (3)0.0022 (19)0.002 (2)0.001 (2)
C200.023 (2)0.012 (3)0.019 (3)0.007 (2)0.004 (2)0.000 (3)
C210.022 (2)0.017 (3)0.018 (3)0.005 (2)0.000 (3)0.001 (2)
C220.022 (3)0.015 (3)0.018 (3)0.000 (2)0.002 (3)0.001 (2)
C230.019 (3)0.016 (2)0.016 (3)0.002 (2)0.000 (2)0.003 (2)
C240.026 (3)0.026 (3)0.025 (3)0.001 (3)0.001 (2)0.001 (3)
C250.024 (3)0.029 (3)0.028 (3)0.004 (3)0.007 (2)0.001 (3)
C260.022 (3)0.024 (3)0.032 (3)0.003 (2)0.006 (3)0.009 (3)
C270.022 (3)0.021 (3)0.028 (3)0.003 (2)0.000 (3)0.003 (2)
C18'0.022 (3)0.017 (2)0.019 (3)0.004 (2)0.002 (3)0.002 (2)
C19'0.022 (2)0.012 (2)0.022 (3)0.0022 (19)0.002 (2)0.001 (2)
C20'0.023 (2)0.012 (3)0.019 (3)0.007 (2)0.004 (2)0.000 (3)
C21'0.022 (2)0.017 (3)0.018 (3)0.005 (2)0.000 (3)0.001 (2)
C22'0.022 (3)0.015 (3)0.018 (3)0.000 (2)0.002 (3)0.001 (2)
C23'0.019 (3)0.016 (2)0.016 (3)0.002 (2)0.000 (2)0.003 (2)
C24'0.026 (3)0.026 (3)0.025 (3)0.001 (3)0.001 (2)0.001 (3)
C25'0.024 (3)0.029 (3)0.028 (3)0.004 (3)0.007 (2)0.001 (3)
C26'0.022 (3)0.024 (3)0.032 (3)0.003 (2)0.006 (3)0.009 (3)
C27'0.022 (3)0.021 (3)0.028 (3)0.003 (2)0.000 (3)0.003 (2)
Geometric parameters (Å, º) top
Sn1—O12.068 (3)C6'—H6'B0.9900
Sn1—C52.143 (4)C7'—C8'1.502 (5)
Sn1—C1'2.149 (18)C7'—H7'A0.9900
Sn1—O22.150 (3)C7'—H7'B0.9900
Sn1—C12.150 (18)C8'—H8'A0.9800
Sn1—N12.192 (3)C8'—H8'B0.9800
Br1—C121.897 (4)C8'—H8'C0.9800
O1—C91.329 (5)C9—C101.409 (6)
O2—C171.292 (6)C9—C141.423 (5)
O3—C201.377 (7)C10—C111.374 (6)
O3—H30.8400C10—H100.9500
O3'—C20'1.388 (7)C11—C121.385 (6)
O3'—H3'0.8400C11—H110.9500
N1—C151.306 (5)C12—C131.369 (6)
N1—N21.396 (5)C13—C141.414 (6)
N2—C171.315 (6)C13—H130.9500
C1—C21.503 (5)C14—C151.462 (5)
C1—H1A0.9900C15—C161.508 (5)
C1—H1B0.9900C16—H16A0.9800
C2—C31.486 (5)C16—H16B0.9800
C2—H2A0.9900C16—H16C0.9800
C2—H2B0.9900C17—C19'1.455 (5)
C3—C41.497 (5)C17—C191.586 (6)
C3—H3A0.9900C18—C191.3900
C3—H3B0.9900C18—C231.3900
C4—H4A0.9800C18—H180.9500
C4—H4B0.9800C19—C201.3900
C4—H4C0.9800C20—C211.3900
C1'—C2'1.498 (5)C21—C221.3900
C1'—H1'A0.9900C21—H210.9500
C1'—H1'B0.9900C22—C231.3900
C2'—C3'1.489 (5)C22—C271.3900
C2'—H2'A0.9900C23—C241.3900
C2'—H2'B0.9900C24—C251.3900
C3'—C4'1.501 (5)C24—H240.9500
C3'—H3'A0.9900C25—C261.3900
C3'—H3'B0.9900C25—H250.9500
C4'—H4'A0.9800C26—C271.3900
C4'—H4'B0.9800C26—H260.9500
C4'—H4'C0.9800C27—H270.9500
C5—C6'1.491 (5)C18'—C19'1.3900
C5—C61.529 (5)C18'—C23'1.3900
C5—H5A0.9900C18'—H18'0.9500
C5—H5B0.9900C19'—C20'1.3900
C5—H5C0.9901C20'—C21'1.3900
C5—H5D0.9901C21'—C22'1.3900
C6—C71.488 (5)C21'—H21'0.9500
C6—H6A0.9900C22'—C23'1.3900
C6—H6B0.9900C22'—C27'1.3900
C7—C81.503 (5)C23'—C24'1.3900
C7—H7A0.9900C24'—C25'1.3900
C7—H7B0.9900C24'—H24'0.9500
C8—H8A0.9800C25'—C26'1.3900
C8—H8B0.9800C25'—H25'0.9500
C8—H8C0.9800C26'—C27'1.3900
C6'—C7'1.490 (5)C26'—H26B0.9500
C6'—H6'A0.9900C27'—H27'0.9500
O1—Sn1—C593.07 (15)C6'—C7'—H7'A110.3
O1—Sn1—C1'103.6 (3)C8'—C7'—H7'A110.3
C5—Sn1—C1'137.3 (3)C6'—C7'—H7'B110.3
O1—Sn1—O2152.85 (12)C8'—C7'—H7'B110.3
C5—Sn1—O293.84 (14)H7'A—C7'—H7'B108.5
C1'—Sn1—O288.8 (3)O1—C9—C10118.2 (4)
O1—Sn1—C196.4 (3)O1—C9—C14122.8 (4)
C5—Sn1—C1129.0 (3)C10—C9—C14119.0 (4)
C1'—Sn1—C112.7 (4)C11—C10—C9121.6 (4)
O2—Sn1—C199.5 (3)C11—C10—H10119.2
O1—Sn1—N181.16 (12)C9—C10—H10119.2
C5—Sn1—N1115.29 (16)C10—C11—C12119.2 (4)
C1'—Sn1—N1106.0 (2)C10—C11—H11120.4
O2—Sn1—N172.15 (12)C12—C11—H11120.4
C1—Sn1—N1115.7 (3)C13—C12—C11121.4 (4)
C9—O1—Sn1122.5 (3)C13—C12—Br1120.1 (3)
C17—O2—Sn1112.4 (3)C11—C12—Br1118.6 (3)
C20—O3—H3120.0C12—C13—C14121.0 (4)
C20'—O3'—H3'120.0C12—C13—H13119.5
C15—N1—N2118.0 (3)C14—C13—H13119.5
C15—N1—Sn1128.5 (3)C13—C14—C9117.9 (4)
N2—N1—Sn1113.5 (2)C13—C14—C15118.8 (4)
C17—N2—N1111.2 (4)C9—C14—C15123.3 (4)
C2—C1—Sn1115.7 (10)N1—C15—C14120.6 (3)
C2—C1—H1A108.4N1—C15—C16119.5 (4)
Sn1—C1—H1A108.4C14—C15—C16119.9 (3)
C2—C1—H1B108.4C15—C16—H16A109.5
Sn1—C1—H1B108.4C15—C16—H16B109.5
H1A—C1—H1B107.4H16A—C16—H16B109.5
C3—C2—C1109.6 (6)C15—C16—H16C109.5
C3—C2—H2A109.8H16A—C16—H16C109.5
C1—C2—H2A109.8H16B—C16—H16C109.5
C3—C2—H2B109.8O2—C17—N2124.2 (4)
C1—C2—H2B109.8O2—C17—C19'110.7 (4)
H2A—C2—H2B108.2N2—C17—C19'125.1 (4)
C2—C3—C4110.0 (6)O2—C17—C19124.1 (4)
C2—C3—H3A109.7N2—C17—C19111.6 (4)
C4—C3—H3A109.7C19—C18—C23120.0
C2—C3—H3B109.7C19—C18—H18120.0
C4—C3—H3B109.7C23—C18—H18120.0
H3A—C3—H3B108.2C20—C19—C18120.0
C2'—C1'—Sn1115.0 (9)C20—C19—C17126.6 (3)
C2'—C1'—H1'A108.5C18—C19—C17113.3 (3)
Sn1—C1'—H1'A108.5O3—C20—C19123.1 (5)
C2'—C1'—H1'B108.5O3—C20—C21116.9 (5)
Sn1—C1'—H1'B108.5C19—C20—C21120.0
H1'A—C1'—H1'B107.5C20—C21—C22120.0
C3'—C2'—C1'110.4 (6)C20—C21—H21120.0
C3'—C2'—H2'A109.6C22—C21—H21120.0
C1'—C2'—H2'A109.6C23—C22—C21120.0
C3'—C2'—H2'B109.6C23—C22—C27120.0
C1'—C2'—H2'B109.6C21—C22—C27120.0
H2'A—C2'—H2'B108.1C24—C23—C22120.0
C2'—C3'—C4'108.3 (6)C24—C23—C18120.0
C2'—C3'—H3'A110.0C22—C23—C18120.0
C4'—C3'—H3'A110.0C23—C24—C25120.0
C2'—C3'—H3'B110.0C23—C24—H24120.0
C4'—C3'—H3'B110.0C25—C24—H24120.0
H3'A—C3'—H3'B108.4C24—C25—C26120.0
C3'—C4'—H4'A109.5C24—C25—H25120.0
C3'—C4'—H4'B109.5C26—C25—H25120.0
H4'A—C4'—H4'B109.5C27—C26—C25120.0
C3'—C4'—H4'C109.5C27—C26—H26120.0
H4'A—C4'—H4'C109.5C25—C26—H26120.0
H4'B—C4'—H4'C109.5C26—C27—C22120.0
C6'—C5—Sn1121.6 (5)C26—C27—H27120.0
C6—C5—Sn1113.2 (4)C22—C27—H27120.0
C6'—C5—H5A119.3C19'—C18'—C23'120.0
C6—C5—H5A108.9C19'—C18'—H18'120.0
Sn1—C5—H5A108.9C23'—C18'—H18'120.0
C6—C5—H5B108.9C20'—C19'—C18'120.0
Sn1—C5—H5B108.9C20'—C19'—C17118.5 (3)
H5A—C5—H5B107.8C18'—C19'—C17121.5 (3)
C6'—C5—H5C108.5O3'—C20'—C19'120.7 (6)
Sn1—C5—H5C106.8O3'—C20'—C21'119.2 (6)
C6'—C5—H5D107.0C19'—C20'—C21'120.0
Sn1—C5—H5D105.5C20'—C21'—C22'120.0
H5C—C5—H5D106.6C20'—C21'—H21'120.0
C7—C6—C5110.8 (5)C22'—C21'—H21'120.0
C7—C6—H6A109.5C23'—C22'—C21'120.0
C5—C6—H6A109.5C23'—C22'—C27'120.0
C7—C6—H6B109.5C21'—C22'—C27'120.0
C5—C6—H6B109.5C24'—C23'—C22'120.0
H6A—C6—H6B108.1C24'—C23'—C18'120.0
C6—C7—C8110.5 (6)C22'—C23'—C18'120.0
C6—C7—H7A109.6C23'—C24'—C25'120.0
C8—C7—H7A109.6C23'—C24'—H24'120.0
C6—C7—H7B109.6C25'—C24'—H24'120.0
C8—C7—H7B109.6C24'—C25'—C26'120.0
H7A—C7—H7B108.1C24'—C25'—H25'120.0
C7'—C6'—C5105.5 (5)C26'—C25'—H25'120.0
C7'—C6'—H6'A110.6C27'—C26'—C25'120.0
C5—C6'—H6'A110.6C27'—C26'—H26B120.0
C7'—C6'—H6'B110.6C25'—C26'—H26B120.0
C5—C6'—H6'B110.6C26'—C27'—C22'120.0
H6'A—C6'—H6'B108.8C26'—C27'—H27'120.0
C6'—C7'—C8'107.2 (5)C22'—C27'—H27'120.0
C5—Sn1—O1—C9162.9 (3)Sn1—N1—C15—C16179.4 (3)
C1'—Sn1—O1—C956.7 (4)C13—C14—C15—N1158.4 (4)
O2—Sn1—O1—C958.3 (4)C9—C14—C15—N122.9 (6)
C1—Sn1—O1—C967.3 (4)C13—C14—C15—C1620.9 (5)
N1—Sn1—O1—C947.8 (3)C9—C14—C15—C16157.8 (4)
O1—Sn1—O2—C1710.0 (4)Sn1—O2—C17—N220.2 (5)
C5—Sn1—O2—C1794.4 (3)Sn1—O2—C17—C19'161.9 (4)
C1'—Sn1—O2—C17128.3 (4)Sn1—O2—C17—C19156.3 (4)
C1—Sn1—O2—C17135.1 (4)N1—N2—C17—O21.2 (6)
N1—Sn1—O2—C1721.0 (3)N1—N2—C17—C19'178.8 (5)
O1—Sn1—N1—C1526.0 (3)N1—N2—C17—C19175.7 (4)
C5—Sn1—N1—C15115.2 (3)C23—C18—C19—C200.0
C1'—Sn1—N1—C1575.7 (5)C23—C18—C19—C17177.2 (4)
O2—Sn1—N1—C15159.1 (4)O2—C17—C19—C20174.3 (3)
C1—Sn1—N1—C1566.9 (5)N2—C17—C19—C202.6 (6)
O1—Sn1—N1—N2153.8 (3)C19'—C17—C19—C20164 (2)
C5—Sn1—N1—N264.6 (3)O2—C17—C19—C188.7 (5)
C1'—Sn1—N1—N2104.5 (4)N2—C17—C19—C18174.4 (3)
O2—Sn1—N1—N221.1 (3)C19'—C17—C19—C1812.8 (18)
C1—Sn1—N1—N2113.3 (4)C18—C19—C20—O3177.5 (6)
C15—N1—N2—C17161.9 (4)C17—C19—C20—O30.7 (6)
Sn1—N1—N2—C1718.2 (4)C18—C19—C20—C210.0
O1—Sn1—C1—C2143.1 (6)C17—C19—C20—C21176.8 (5)
C5—Sn1—C1—C243.9 (8)O3—C20—C21—C22177.7 (6)
C1'—Sn1—C1—C292 (3)C19—C20—C21—C220.0
O2—Sn1—C1—C259.0 (7)C20—C21—C22—C230.0
N1—Sn1—C1—C2133.7 (6)C20—C21—C22—C27180.0
Sn1—C1—C2—C370.2 (9)C21—C22—C23—C24180.0
C1—C2—C3—C4174.7 (10)C27—C22—C23—C240.0
O1—Sn1—C1'—C2'84.1 (7)C21—C22—C23—C180.0
C5—Sn1—C1'—C2'26.0 (10)C27—C22—C23—C18180.0
O2—Sn1—C1'—C2'120.3 (7)C19—C18—C23—C24180.0
C1—Sn1—C1'—C2'27.5 (19)C19—C18—C23—C220.0
N1—Sn1—C1'—C2'168.6 (6)C22—C23—C24—C250.0
Sn1—C1'—C2'—C3'60.8 (10)C18—C23—C24—C25180.0
C1'—C2'—C3'—C4'177.9 (10)C23—C24—C25—C260.0
O1—Sn1—C5—C6'146.5 (4)C24—C25—C26—C270.0
C1'—Sn1—C5—C6'99.6 (6)C25—C26—C27—C220.0
O2—Sn1—C5—C6'7.3 (4)C23—C22—C27—C260.0
C1—Sn1—C5—C6'112.8 (5)C21—C22—C27—C26180.0
N1—Sn1—C5—C6'64.8 (5)C23'—C18'—C19'—C20'0.0
O1—Sn1—C5—C6170.1 (5)C23'—C18'—C19'—C17179.2 (5)
C1'—Sn1—C5—C676.0 (7)O2—C17—C19'—C20'179.0 (3)
O2—Sn1—C5—C616.4 (5)N2—C17—C19'—C20'3.0 (7)
C1—Sn1—C5—C689.1 (6)C19—C17—C19'—C20'18.0 (17)
N1—Sn1—C5—C688.4 (5)O2—C17—C19'—C18'0.1 (5)
C6'—C5—C6—C758.2 (13)N2—C17—C19'—C18'177.8 (3)
Sn1—C5—C6—C7175.5 (6)C19—C17—C19'—C18'161 (2)
C5—C6—C7—C8177.9 (7)C18'—C19'—C20'—O3'177.0 (6)
C6—C5—C6'—C7'8.5 (11)C17—C19'—C20'—O3'3.8 (6)
Sn1—C5—C6'—C7'82.3 (7)C18'—C19'—C20'—C21'0.0
C5—C6'—C7'—C8'177.6 (7)C17—C19'—C20'—C21'179.2 (5)
Sn1—O1—C9—C10137.7 (3)O3'—C20'—C21'—C22'177.1 (6)
Sn1—O1—C9—C1445.5 (5)C19'—C20'—C21'—C22'0.0
O1—C9—C10—C11177.8 (4)C20'—C21'—C22'—C23'0.0
C14—C9—C10—C111.0 (6)C20'—C21'—C22'—C27'180.0
C9—C10—C11—C120.8 (6)C21'—C22'—C23'—C24'180.0
C10—C11—C12—C130.7 (6)C27'—C22'—C23'—C24'0.0
C10—C11—C12—Br1179.6 (3)C21'—C22'—C23'—C18'0.0
C11—C12—C13—C140.8 (6)C27'—C22'—C23'—C18'180.0
Br1—C12—C13—C14179.4 (3)C19'—C18'—C23'—C24'180.0
C12—C13—C14—C91.0 (6)C19'—C18'—C23'—C22'0.0
C12—C13—C14—C15177.8 (4)C22'—C23'—C24'—C25'0.0
O1—C9—C14—C13177.8 (4)C18'—C23'—C24'—C25'180.0
C10—C9—C14—C131.1 (6)C23'—C24'—C25'—C26'0.0
O1—C9—C14—C151.0 (6)C24'—C25'—C26'—C27'0.0
C10—C9—C14—C15177.7 (4)C25'—C26'—C27'—C22'0.0
N2—N1—C15—C14178.9 (3)C23'—C22'—C27'—C26'0.0
Sn1—N1—C15—C141.2 (5)C21'—C22'—C27'—C26'180.0
N2—N1—C15—C160.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N20.842.072.696 (11)131
O3—H3···N20.841.882.546 (12)136

Experimental details

Crystal data
Chemical formula[Sn(C4H9)2(C19H13BrN2O3)]
Mr630.14
Crystal system, space groupMonoclinic, P21/c
Temperature (K)140
a, b, c (Å)14.2649 (2), 7.2249 (1), 24.9527 (3)
β (°) 95.483 (1)
V3)2559.92 (6)
Z4
Radiation typeMo Kα
µ (mm1)2.59
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.424, 0.625
No. of measured, independent and
observed [I > 2σ(I)] reflections
23522, 5885, 5168
Rint0.031
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.114, 1.26
No. of reflections5885
No. of parameters318
No. of restraints160
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.36, 1.07

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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