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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m862.
Published online 2009 July 4. doi:  10.1107/S1600536809024477
PMCID: PMC2977471

[N′-(5-Bromo-2-oxidobenzyl­idene-κO)-3-hydr­oxy-2-naphthohydrazidato-κ2 N′,O]dibutyl­tin(IV)

Abstract

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0m862-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C18H11BrN2O3)]
  • M r = 616.11
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m862-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 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 [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/S1600536809024477/xu2544sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024477/xu2544Isup2.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 (0.39 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

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.

Figures

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.

Crystal data

[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

Bruker SMART APEX diffractometer5740 independent reflections
Radiation source: fine-focus sealed tube4886 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.515, Tmax = 0.621k = −15→15
12053 measured reflectionsl = −16→16

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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 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

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

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)
H180.55660.6618−0.00060.032*
C190.3555 (3)0.7338 (2)−0.08373 (19)0.0290 (5)
C200.3883 (3)0.6414 (2)−0.1309 (2)0.0339 (5)
H200.48470.5757−0.11880.041*
C210.2825 (3)0.6461 (3)−0.1935 (2)0.0408 (6)
H210.30470.5829−0.22340.049*
C220.1397 (3)0.7457 (3)−0.2134 (2)0.0397 (6)
H220.06650.7484−0.25680.048*
C230.1049 (3)0.8378 (3)−0.1720 (2)0.0348 (5)
H230.00860.9047−0.18790.042*
C240.2118 (2)0.8345 (2)−0.1049 (2)0.0292 (5)
C250.1806 (2)0.9263 (2)−0.0580 (2)0.0304 (5)
H250.08510.9945−0.07310.036*
C260.2844 (2)0.9195 (2)0.0086 (2)0.0290 (5)

Atomic displacement parameters (Å2)

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, °)

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—C15−9.94 (19)C9—C10—C11—C12−1.4 (4)
C1—Sn1—N1—C15−94.8 (4)C10—C11—C12—C130.8 (4)
C5—Sn1—N1—C1585.7 (2)C10—C11—C12—Br1−178.50 (18)
O2—Sn1—N1—C15177.7 (2)C11—C12—C13—C140.6 (3)
C1'—Sn1—N1—C15−105.6 (5)Br1—C12—C13—C14179.89 (16)
O1—Sn1—N1—N2173.53 (15)C12—C13—C14—C9−1.4 (3)
C1—Sn1—N1—N288.7 (4)C12—C13—C14—C15179.8 (2)
C5—Sn1—N1—N2−90.79 (15)O1—C9—C14—C13−177.6 (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—C16−178.12 (19)C10—C9—C14—C15179.5 (2)
Sn1—N1—N2—C16−1.1 (2)N2—N1—C15—C14178.17 (19)
C1—Sn1—O1—C9146.5 (3)Sn1—N1—C15—C141.6 (3)
C5—Sn1—O1—C9−87.0 (2)C13—C14—C15—N1−175.1 (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—C17−178.28 (14)
O1—Sn1—O2—C16−18.6 (2)N1—N2—C16—O20.2 (3)
C1—Sn1—O2—C16−128.4 (3)N1—N2—C16—C17179.36 (17)
C5—Sn1—O2—C16103.52 (16)O2—C16—C17—C18−0.9 (3)
C1'—Sn1—O2—C16−128.1 (3)N2—C16—C17—C18179.84 (19)
N1—Sn1—O2—C16−1.07 (14)O2—C16—C17—C26177.4 (2)
O1—Sn1—C1—C2137.0 (6)N2—C16—C17—C26−1.8 (3)
C5—Sn1—C1—C237.3 (8)C26—C17—C18—C19−0.9 (3)
O2—Sn1—C1—C2−67.4 (7)C16—C17—C18—C19177.48 (19)
C1'—Sn1—C1—C2−69 (3)C17—C18—C19—C20−179.3 (2)
N1—Sn1—C1—C2−142.1 (5)C17—C18—C19—C240.1 (3)
Sn1—C1—C2—C3−59.5 (10)C18—C19—C20—C21177.6 (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—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—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—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—C25−179.7 (2)
O1—Sn1—C5—C668.73 (16)C18—C19—C24—C23−178.6 (2)
C1—Sn1—C5—C6165.0 (4)C20—C19—C24—C230.8 (3)
O2—Sn1—C5—C6−89.24 (16)C23—C24—C25—C26178.5 (2)
C1'—Sn1—C5—C6176.3 (5)C19—C24—C25—C26−1.0 (3)
N1—Sn1—C5—C6−15.50 (18)C24—C25—C26—O3179.3 (2)
Sn1—C5—C6—C7−179.63 (15)C24—C25—C26—C170.1 (3)
C5—C6—C7—C8−179.5 (2)C18—C17—C26—O3−178.3 (2)
Sn1—O1—C9—C10164.47 (17)C16—C17—C26—O33.3 (3)
Sn1—O1—C9—C14−17.1 (3)C18—C17—C26—C250.8 (3)
O1—C9—C10—C11179.1 (2)C16—C17—C26—C25−177.5 (2)
C14—C9—C10—C110.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N20.83 (1)1.88 (2)2.606 (2)146 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2544).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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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