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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m863.
Published online 2009 July 4. doi:  10.1107/S160053680902457X
PMCID: PMC2977220

{N′-[1-(5-Bromo-2-oxidophenyl-κO)ethyl­idene]-3-hydroxy-2-naphtho­hydrazidato-κ2 N′,O}dibutyl­tin(IV)

Abstract

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 [triangle]); Samanta et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m863-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C19H13BrN2O3)]
  • M r = 630.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m863-efi1.jpg
  • 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 [triangle]) T min = 0.424, T max = 0.625
  • 23522 measured reflections
  • 5885 independent reflections
  • 5168 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902457X/xu2545sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902457X/xu2545Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

[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

Bruker SMART APEX diffractometer5885 independent reflections
Radiation source: fine-focus sealed tube5168 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→18
Tmin = 0.424, Tmax = 0.625k = −9→9
23522 measured reflectionsl = −32→32

Refinement

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 = 1.26w = 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

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

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
H8A0.4533−0.00800.52600.055*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)

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, °)

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—C9−162.9 (3)Sn1—N1—C15—C16−179.4 (3)
C1'—Sn1—O1—C956.7 (4)C13—C14—C15—N1158.4 (4)
O2—Sn1—O1—C9−58.3 (4)C9—C14—C15—N1−22.9 (6)
C1—Sn1—O1—C967.3 (4)C13—C14—C15—C16−20.9 (5)
N1—Sn1—O1—C9−47.8 (3)C9—C14—C15—C16157.8 (4)
O1—Sn1—O2—C17−10.0 (4)Sn1—O2—C17—N220.2 (5)
C5—Sn1—O2—C1794.4 (3)Sn1—O2—C17—C19'−161.9 (4)
C1'—Sn1—O2—C17−128.3 (4)Sn1—O2—C17—C19−156.3 (4)
C1—Sn1—O2—C17−135.1 (4)N1—N2—C17—O2−1.2 (6)
N1—Sn1—O2—C17−21.0 (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—C15−75.7 (5)C23—C18—C19—C17−177.2 (4)
O2—Sn1—N1—C15−159.1 (4)O2—C17—C19—C20174.3 (3)
C1—Sn1—N1—C15−66.9 (5)N2—C17—C19—C20−2.6 (6)
O1—Sn1—N1—N2−153.8 (3)C19'—C17—C19—C20−164 (2)
C5—Sn1—N1—N2−64.6 (3)O2—C17—C19—C18−8.7 (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—O3−177.5 (6)
C15—N1—N2—C17161.9 (4)C17—C19—C20—O3−0.7 (6)
Sn1—N1—N2—C17−18.2 (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—C2−92 (3)C19—C20—C21—C220.0
O2—Sn1—C1—C2−59.0 (7)C20—C21—C22—C230.0
N1—Sn1—C1—C2−133.7 (6)C20—C21—C22—C27180.0
Sn1—C1—C2—C3−70.2 (9)C21—C22—C23—C24180.0
C1—C2—C3—C4−174.7 (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—C6−76.0 (7)O2—C17—C19'—C20'179.0 (3)
O2—Sn1—C5—C616.4 (5)N2—C17—C19'—C20'−3.0 (7)
C1—Sn1—C5—C6−89.1 (6)C19—C17—C19'—C20'18.0 (17)
N1—Sn1—C5—C688.4 (5)O2—C17—C19'—C18'−0.1 (5)
C6'—C5—C6—C7−58.2 (13)N2—C17—C19'—C18'177.8 (3)
Sn1—C5—C6—C7−175.5 (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—C10−137.7 (3)O3'—C20'—C21'—C22'177.1 (6)
Sn1—O1—C9—C1445.5 (5)C19'—C20'—C21'—C22'0.0
O1—C9—C10—C11−177.8 (4)C20'—C21'—C22'—C23'0.0
C14—C9—C10—C11−1.0 (6)C20'—C21'—C22'—C27'180.0
C9—C10—C11—C120.8 (6)C21'—C22'—C23'—C24'180.0
C10—C11—C12—C13−0.7 (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—C14−179.4 (3)C19'—C18'—C23'—C24'180.0
C12—C13—C14—C9−1.0 (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—C15−1.0 (6)C24'—C25'—C26'—C27'0.0
C10—C9—C14—C15−177.7 (4)C25'—C26'—C27'—C22'0.0
N2—N1—C15—C14−178.9 (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, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N20.842.072.696 (11)131
O3'—H3'···N20.841.882.546 (12)136

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2545).

References

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  • Labib, L., Khalil, T. E., Iskander, M. F. & Refaat, L. S. (1996). Polyhedron, 21, 3697–3707.
  • Samanta, B., Chakraborty, J., Dey, D. K. & Mitra, S. (2007). Struct. Chem.18, 287–297.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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