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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 May 7;67(Pt 6):m710. doi: 10.1107/S1600536811016436

catena-Poly[[tribenzyl­tin(IV)]-μ-4-formyl-2-meth­oxy-6-nitro­phenolato-κ2 O 1:O 4]

Thy Chun Keng a, Kong Mun Lo a, Seik Weng Ng a,*
PMCID: PMC3120579  PMID: 21754610

Abstract

The formyl­meth­oxy­nitro­phenoxide ions in the polymeric title compound, [Sn(C7H7)3(C8H6NO5)]n, link adjacent triorganotin(IV) cations into linear chains lying close to (101) [Sn—O = 2.1227 (12) Å and Sn← O = 2.4936 (13) Å]. The SnIV atom is displaced out of the C3Sn girdle of the trans-C3SnO2 trigonal-bipyramidal polyhedron in the direction of the covalently-bonded O atom [Sn—O—C = 137.63 (11)°] by 0.247 (1) Å; the geometry is distorted towards an octa­hedron by a remote O atom of the meth­oxy subsituent [Sn⋯O = 3.019 (1) Å]

Related literature

For a related structure, see: James et al. (1998 ▶). For a description of triorganotin phenoxides, see: Poller (1970 ▶).graphic file with name e-67-0m710-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H7)3(C8H6NO5)]

  • M r = 588.21

  • Monoclinic, Inline graphic

  • a = 12.1241 (1) Å

  • b = 16.5829 (2) Å

  • c = 13.3893 (2) Å

  • β = 106.3701 (6)°

  • V = 2582.83 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.03 mm−1

  • T = 100 K

  • 0.25 × 0.25 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.783, T max = 0.904

  • 25760 measured reflections

  • 6372 independent reflections

  • 5545 reflections with I > 2σ(I)

  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024

  • wR(F 2) = 0.063

  • S = 1.01

  • 6372 reflections

  • 325 parameters

  • H-atom parameters constrained

  • Δρmax = 1.02 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016436/jh2283sup1.cif

e-67-0m710-sup1.cif (23.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016436/jh2283Isup2.hkl

e-67-0m710-Isup2.hkl (311.9KB, hkl)

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

Acknowledgments

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

Triorganotin alkoxides are compounds, unlike triorganotin phenoxides, which are generally not stable in air, as stated in a textbook on organotin chemistry (Poller, 1970). As such, there are few reports on phenoxides. Vanillin and its derivatives possess a hydroxy group that can be deprotonated; the 5-nitrovallinate anion in polymeric [Sn(C7H7)3(C8H7NO5)]n (Scheme I) links adjacent triorganotin(IV) cations to form a linear chain running along the a–c diagonal of the monoclinic unit cell (Fig. 1). The dative Sn–O bond is significantly longer than the covalent Sn–O bond [Sn–O 2.123 (1), Sn←O 2.494 (1) Å], so that the SnIV atom is displaced out of the C3Sn girdle of the trans-C3SnO2 trigonal bipyramidal polyhedron in the direction of the covalently-bonded O atom [Sn–O–C 137.6 (1) Å] by 0.247 (1) Å. The geometry is distorted towards an octahedron by the O atom of the methoxy subsituent [Sn···O 3.019 (1) Å]. There are few examples of triorganotin systems having Sn←Oaromatic aldehdye bond; one example is triphenyltin salicylaldehydate, which features a long Sn←O bond (James et al., 1998).

Experimental

Tribenzyltin hydroxide was prepared by the base hydrolysis of tribenzyl)tin chloride with 10% sodium hydroxide solution. The compound (0.41 g, 1 mmol) hydroxide and 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (5-nitrovanillin) (0.2 g, 1 mmol) were dissolved in ethanol (100 ml) and the mixture was heated for an hour. The solution was filtered and the solvent allowed to evaporate for a few days.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 times Ueq(C). The final difference Fourier map had a peak in the vicinity of Sn1.

Figures

Fig. 1.

Fig. 1.

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Thermal ellipsoid plot (Barbour, 2001) of a portion of the chain structure of Sn(C7H7)3(C8H6NO5) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Sn(C7H7)3(C8H6NO5)] F(000) = 1192
Mr = 588.21 Dx = 1.513 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 9964 reflections
a = 12.1241 (1) Å θ = 2.4–28.2°
b = 16.5829 (2) Å µ = 1.03 mm−1
c = 13.3893 (2) Å T = 100 K
β = 106.3701 (6)° Block, colorless
V = 2582.83 (5) Å3 0.25 × 0.25 × 0.10 mm
Z = 4
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Data collection

Bruker SMART APEX diffractometer 6372 independent reflections
Radiation source: fine-focus sealed tube 5545 reflections with I > 2σ(I)
graphite Rint = 0.028
ω scans θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −16→16
Tmin = 0.783, Tmax = 0.904 k = −22→21
25760 measured reflections l = −17→17
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Refinement

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)] = 0.024 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063 H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0349P)2 + 0.888P] where P = (Fo2 + 2Fc2)/3
6372 reflections (Δ/σ)max = 0.001
325 parameters Δρmax = 1.02 e Å−3
0 restraints Δρmin = −0.25 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Sn1 0.368458 (10) 0.189545 (7) 0.722727 (9) 0.01643 (5)
O1 0.27411 (11) 0.13103 (7) 0.81338 (10) 0.0204 (3)
O2 0.28459 (11) 0.27891 (8) 0.88378 (11) 0.0218 (3)
O3 −0.01389 (12) 0.27479 (8) 1.10347 (11) 0.0262 (3)
O4 0.04948 (13) −0.03179 (8) 0.87527 (11) 0.0296 (3)
O5 0.15153 (15) −0.00208 (10) 0.77303 (13) 0.0426 (4)
N1 0.10833 (14) 0.01628 (9) 0.84212 (12) 0.0218 (3)
C1 0.38886 (16) 0.07215 (11) 0.66076 (14) 0.0209 (4)
H1A 0.4702 0.0645 0.6619 0.025*
H1B 0.3691 0.0300 0.7052 0.025*
C2 0.31382 (16) 0.06304 (11) 0.55183 (14) 0.0215 (4)
C3 0.3568 (2) 0.07057 (14) 0.46631 (17) 0.0343 (5)
H3 0.4368 0.0790 0.4768 0.041*
C4 0.2842 (2) 0.06586 (17) 0.36588 (18) 0.0449 (6)
H4 0.3150 0.0714 0.3084 0.054*
C5 0.1676 (2) 0.05316 (15) 0.34835 (18) 0.0411 (6)
H5 0.1183 0.0501 0.2793 0.049*
C6 0.12380 (18) 0.04503 (12) 0.43205 (18) 0.0315 (5)
H6 0.0438 0.0361 0.4208 0.038*
C7 0.19544 (17) 0.04974 (11) 0.53232 (16) 0.0245 (4)
H7 0.1639 0.0439 0.5893 0.029*
C8 0.23785 (17) 0.26471 (12) 0.62210 (16) 0.0250 (4)
H8A 0.2716 0.3188 0.6193 0.030*
H8B 0.2191 0.2419 0.5510 0.030*
C9 0.12731 (16) 0.27558 (12) 0.65014 (14) 0.0215 (4)
C10 0.05093 (18) 0.21194 (12) 0.64538 (16) 0.0263 (4)
H10 0.0688 0.1603 0.6236 0.032*
C11 −0.05074 (17) 0.22273 (14) 0.67194 (17) 0.0305 (4)
H11 −0.1013 0.1785 0.6689 0.037*
C12 −0.07859 (19) 0.29776 (14) 0.70286 (18) 0.0350 (5)
H12 −0.1483 0.3053 0.7209 0.042*
C13 −0.00443 (18) 0.36165 (13) 0.70734 (18) 0.0325 (5)
H13 −0.0233 0.4133 0.7285 0.039*
C14 0.09776 (17) 0.35095 (12) 0.68101 (15) 0.0259 (4)
H14 0.1479 0.3955 0.6841 0.031*
C15 0.51642 (16) 0.22724 (12) 0.84500 (15) 0.0242 (4)
H15A 0.5502 0.2766 0.8240 0.029*
H15B 0.4943 0.2391 0.9092 0.029*
C16 0.60161 (16) 0.15935 (12) 0.86363 (14) 0.0221 (4)
C17 0.59103 (17) 0.09386 (12) 0.92531 (15) 0.0264 (4)
H17 0.5317 0.0937 0.9589 0.032*
C18 0.66561 (18) 0.02880 (13) 0.93860 (16) 0.0305 (4)
H18 0.6574 −0.0152 0.9814 0.037*
C19 0.75189 (19) 0.02786 (15) 0.88964 (17) 0.0346 (5)
H19 0.8027 −0.0169 0.8981 0.042*
C20 0.76353 (18) 0.09220 (15) 0.82865 (17) 0.0368 (5)
H20 0.8227 0.0917 0.7949 0.044*
C21 0.69000 (17) 0.15770 (14) 0.81585 (17) 0.0303 (4)
H21 0.6999 0.2019 0.7741 0.036*
C22 0.20411 (15) 0.15092 (11) 0.86575 (13) 0.0170 (3)
C23 0.20697 (15) 0.23057 (11) 0.91021 (14) 0.0186 (3)
C24 0.13811 (15) 0.25138 (11) 0.97130 (14) 0.0198 (4)
H24 0.1428 0.3039 1.0007 0.024*
C25 0.05980 (16) 0.19419 (11) 0.99044 (14) 0.0204 (4)
C26 0.05257 (16) 0.11815 (11) 0.94786 (14) 0.0202 (4)
H26 −0.0005 0.0802 0.9607 0.024*
C27 0.12282 (15) 0.09688 (10) 0.88604 (14) 0.0180 (3)
C28 −0.01506 (17) 0.21211 (12) 1.05483 (16) 0.0246 (4)
H28 −0.0694 0.1721 1.0597 0.030*
C29 0.28924 (18) 0.36164 (11) 0.91567 (16) 0.0258 (4)
H29A 0.3482 0.3900 0.8920 0.039*
H29B 0.3083 0.3645 0.9917 0.039*
H29C 0.2143 0.3871 0.8851 0.039*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Sn1 0.01783 (7) 0.01555 (7) 0.01806 (7) 0.00019 (4) 0.00854 (5) 0.00098 (4)
O1 0.0242 (7) 0.0177 (6) 0.0241 (7) 0.0014 (5) 0.0149 (5) 0.0016 (5)
O2 0.0257 (7) 0.0157 (6) 0.0285 (7) −0.0025 (5) 0.0148 (6) −0.0009 (5)
O3 0.0320 (8) 0.0237 (7) 0.0289 (7) 0.0005 (6) 0.0183 (6) −0.0035 (6)
O4 0.0402 (8) 0.0228 (7) 0.0312 (8) −0.0108 (6) 0.0186 (6) −0.0012 (6)
O5 0.0593 (11) 0.0319 (9) 0.0528 (11) −0.0168 (7) 0.0424 (9) −0.0188 (7)
N1 0.0243 (8) 0.0199 (8) 0.0224 (8) −0.0030 (6) 0.0088 (6) −0.0005 (6)
C1 0.0230 (9) 0.0198 (9) 0.0219 (9) 0.0019 (7) 0.0098 (7) −0.0002 (7)
C2 0.0256 (9) 0.0164 (8) 0.0234 (9) 0.0004 (7) 0.0087 (7) −0.0003 (7)
C3 0.0347 (12) 0.0426 (13) 0.0299 (11) −0.0121 (10) 0.0160 (9) −0.0065 (10)
C4 0.0574 (16) 0.0559 (16) 0.0255 (11) −0.0199 (13) 0.0183 (11) −0.0060 (11)
C5 0.0479 (14) 0.0404 (13) 0.0281 (11) −0.0067 (11) −0.0004 (10) −0.0039 (10)
C6 0.0280 (11) 0.0240 (10) 0.0402 (12) 0.0007 (8) 0.0056 (9) −0.0034 (9)
C7 0.0276 (10) 0.0176 (9) 0.0309 (10) 0.0012 (7) 0.0125 (8) −0.0024 (8)
C8 0.0273 (10) 0.0257 (10) 0.0260 (10) 0.0064 (8) 0.0138 (8) 0.0070 (8)
C9 0.0225 (9) 0.0246 (9) 0.0184 (9) 0.0054 (7) 0.0076 (7) 0.0040 (7)
C10 0.0304 (11) 0.0248 (10) 0.0231 (10) 0.0025 (8) 0.0066 (8) −0.0007 (8)
C11 0.0239 (10) 0.0359 (11) 0.0307 (11) −0.0049 (9) 0.0060 (8) −0.0004 (9)
C12 0.0213 (10) 0.0457 (13) 0.0403 (13) 0.0029 (9) 0.0125 (9) −0.0038 (10)
C13 0.0292 (11) 0.0290 (11) 0.0409 (12) 0.0078 (9) 0.0125 (9) −0.0032 (9)
C14 0.0258 (10) 0.0240 (10) 0.0284 (10) 0.0040 (8) 0.0086 (8) 0.0021 (8)
C15 0.0236 (10) 0.0229 (9) 0.0271 (10) −0.0038 (8) 0.0089 (8) −0.0062 (8)
C16 0.0178 (9) 0.0262 (9) 0.0211 (9) −0.0029 (7) 0.0036 (7) −0.0053 (8)
C17 0.0224 (10) 0.0328 (11) 0.0234 (10) −0.0047 (8) 0.0059 (7) −0.0014 (8)
C18 0.0272 (10) 0.0323 (11) 0.0279 (10) −0.0001 (8) 0.0009 (8) 0.0028 (9)
C19 0.0285 (11) 0.0413 (13) 0.0297 (11) 0.0103 (9) 0.0013 (9) −0.0015 (10)
C20 0.0227 (10) 0.0572 (15) 0.0321 (11) 0.0088 (10) 0.0106 (9) 0.0027 (11)
C21 0.0227 (10) 0.0398 (12) 0.0299 (11) −0.0001 (9) 0.0096 (8) 0.0061 (9)
C22 0.0193 (9) 0.0181 (9) 0.0143 (8) 0.0024 (7) 0.0056 (6) 0.0027 (7)
C23 0.0197 (9) 0.0172 (8) 0.0197 (9) 0.0003 (7) 0.0071 (7) 0.0035 (7)
C24 0.0244 (9) 0.0172 (8) 0.0191 (9) 0.0011 (7) 0.0084 (7) 0.0003 (7)
C25 0.0227 (9) 0.0221 (9) 0.0194 (9) 0.0015 (7) 0.0110 (7) 0.0015 (7)
C26 0.0209 (9) 0.0206 (9) 0.0220 (9) −0.0010 (7) 0.0106 (7) 0.0025 (7)
C27 0.0213 (9) 0.0155 (8) 0.0182 (8) 0.0000 (7) 0.0072 (7) −0.0004 (7)
C28 0.0274 (10) 0.0223 (9) 0.0291 (10) 0.0002 (8) 0.0159 (8) 0.0017 (8)
C29 0.0318 (11) 0.0165 (9) 0.0313 (10) −0.0043 (8) 0.0125 (8) −0.0019 (8)
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Geometric parameters (Å, °)

Sn1—O1 2.1227 (12) C11—C12 1.383 (3)
Sn1—C15 2.1526 (19) C11—H11 0.9500
Sn1—C1 2.1576 (18) C12—C13 1.380 (3)
Sn1—C8 2.1619 (19) C12—H12 0.9500
Sn1—O3i 2.4936 (13) C13—C14 1.392 (3)
O1—C22 1.287 (2) C13—H13 0.9500
O2—C23 1.357 (2) C14—H14 0.9500
O2—C29 1.433 (2) C15—C16 1.500 (3)
O3—C28 1.225 (2) C15—H15A 0.9900
O3—Sn1ii 2.4936 (13) C15—H15B 0.9900
O4—N1 1.233 (2) C16—C17 1.392 (3)
O5—N1 1.223 (2) C16—C21 1.395 (3)
N1—C27 1.451 (2) C17—C18 1.387 (3)
C1—C2 1.493 (3) C17—H17 0.9500
C1—H1A 0.9900 C18—C19 1.382 (3)
C1—H1B 0.9900 C18—H18 0.9500
C2—C3 1.391 (3) C19—C20 1.375 (3)
C2—C7 1.402 (3) C19—H19 0.9500
C3—C4 1.386 (3) C20—C21 1.385 (3)
C3—H3 0.9500 C20—H20 0.9500
C4—C5 1.382 (4) C21—H21 0.9500
C4—H4 0.9500 C22—C27 1.414 (2)
C5—C6 1.375 (3) C22—C23 1.445 (3)
C5—H5 0.9500 C23—C24 1.367 (2)
C6—C7 1.380 (3) C24—C25 1.416 (2)
C6—H6 0.9500 C24—H24 0.9500
C7—H7 0.9500 C25—C26 1.377 (3)
C8—C9 1.501 (3) C25—C28 1.448 (3)
C8—H8A 0.9900 C26—C27 1.390 (2)
C8—H8B 0.9900 C26—H26 0.9500
C9—C10 1.394 (3) C28—H28 0.9500
C9—C14 1.395 (3) C29—H29A 0.9800
C10—C11 1.387 (3) C29—H29B 0.9800
C10—H10 0.9500 C29—H29C 0.9800
O1—Sn1—C15 99.54 (6) C12—C13—C14 120.5 (2)
O1—Sn1—C1 86.91 (6) C12—C13—H13 119.8
C15—Sn1—C1 113.15 (7) C14—C13—H13 119.8
O1—Sn1—C8 101.64 (6) C13—C14—C9 120.71 (19)
C15—Sn1—C8 127.85 (8) C13—C14—H14 119.6
C1—Sn1—C8 115.07 (8) C9—C14—H14 119.6
O1—Sn1—O3i 166.47 (5) C16—C15—Sn1 107.19 (12)
C15—Sn1—O3i 85.05 (6) C16—C15—H15A 110.3
C1—Sn1—O3i 79.60 (6) Sn1—C15—H15A 110.3
C8—Sn1—O3i 85.12 (6) C16—C15—H15B 110.3
C22—O1—Sn1 137.63 (11) Sn1—C15—H15B 110.3
C23—O2—C29 117.37 (14) H15A—C15—H15B 108.5
C28—O3—Sn1ii 128.23 (13) C17—C16—C21 117.91 (19)
O5—N1—O4 121.74 (16) C17—C16—C15 120.65 (17)
O5—N1—C27 120.47 (15) C21—C16—C15 121.36 (18)
O4—N1—C27 117.77 (15) C16—C17—C18 121.16 (19)
C2—C1—Sn1 111.26 (12) C16—C17—H17 119.4
C2—C1—H1A 109.4 C18—C17—H17 119.4
Sn1—C1—H1A 109.4 C19—C18—C17 120.1 (2)
C2—C1—H1B 109.4 C19—C18—H18 120.0
Sn1—C1—H1B 109.4 C17—C18—H18 120.0
H1A—C1—H1B 108.0 C20—C19—C18 119.4 (2)
C3—C2—C7 117.52 (18) C20—C19—H19 120.3
C3—C2—C1 121.91 (17) C18—C19—H19 120.3
C7—C2—C1 120.52 (17) C19—C20—C21 120.8 (2)
C4—C3—C2 120.7 (2) C19—C20—H20 119.6
C4—C3—H3 119.6 C21—C20—H20 119.6
C2—C3—H3 119.6 C20—C21—C16 120.6 (2)
C5—C4—C3 120.8 (2) C20—C21—H21 119.7
C5—C4—H4 119.6 C16—C21—H21 119.7
C3—C4—H4 119.6 O1—C22—C27 123.00 (16)
C6—C5—C4 119.2 (2) O1—C22—C23 121.05 (16)
C6—C5—H5 120.4 C27—C22—C23 115.93 (15)
C4—C5—H5 120.4 O2—C23—C24 126.31 (17)
C5—C6—C7 120.4 (2) O2—C23—C22 111.73 (15)
C5—C6—H6 119.8 C24—C23—C22 121.95 (16)
C7—C6—H6 119.8 C23—C24—C25 119.54 (17)
C6—C7—C2 121.38 (19) C23—C24—H24 120.2
C6—C7—H7 119.3 C25—C24—H24 120.2
C2—C7—H7 119.3 C26—C25—C24 120.43 (17)
C9—C8—Sn1 117.52 (13) C26—C25—C28 117.20 (17)
C9—C8—H8A 107.9 C24—C25—C28 122.37 (17)
Sn1—C8—H8A 107.9 C25—C26—C27 120.06 (17)
C9—C8—H8B 107.9 C25—C26—H26 120.0
Sn1—C8—H8B 107.9 C27—C26—H26 120.0
H8A—C8—H8B 107.2 C26—C27—C22 122.06 (16)
C10—C9—C14 118.00 (18) C26—C27—N1 116.78 (16)
C10—C9—C8 121.76 (18) C22—C27—N1 121.16 (15)
C14—C9—C8 120.25 (18) O3—C28—C25 125.14 (18)
C11—C10—C9 121.16 (19) O3—C28—H28 117.4
C11—C10—H10 119.4 C25—C28—H28 117.4
C9—C10—H10 119.4 O2—C29—H29A 109.5
C12—C11—C10 120.2 (2) O2—C29—H29B 109.5
C12—C11—H11 119.9 H29A—C29—H29B 109.5
C10—C11—H11 119.9 O2—C29—H29C 109.5
C13—C12—C11 119.5 (2) H29A—C29—H29C 109.5
C13—C12—H12 120.2 H29B—C29—H29C 109.5
C11—C12—H12 120.2
C15—Sn1—O1—C22 83.51 (18) Sn1—C15—C16—C21 95.27 (19)
C1—Sn1—O1—C22 −163.52 (18) C21—C16—C17—C18 −0.3 (3)
C8—Sn1—O1—C22 −48.54 (18) C15—C16—C17—C18 176.55 (18)
O3i—Sn1—O1—C22 −167.57 (18) C16—C17—C18—C19 −0.5 (3)
O1—Sn1—C1—C2 105.81 (13) C17—C18—C19—C20 0.6 (3)
C15—Sn1—C1—C2 −155.13 (12) C18—C19—C20—C21 0.0 (3)
C8—Sn1—C1—C2 4.40 (15) C19—C20—C21—C16 −0.8 (3)
O3i—Sn1—C1—C2 −75.15 (13) C17—C16—C21—C20 0.9 (3)
Sn1—C1—C2—C3 101.24 (19) C15—C16—C21—C20 −175.92 (19)
Sn1—C1—C2—C7 −76.10 (19) Sn1—O1—C22—C27 155.51 (14)
C7—C2—C3—C4 0.7 (3) Sn1—O1—C22—C23 −26.3 (3)
C1—C2—C3—C4 −176.7 (2) C29—O2—C23—C24 −5.3 (3)
C2—C3—C4—C5 −0.3 (4) C29—O2—C23—C22 174.93 (15)
C3—C4—C5—C6 −0.1 (4) O1—C22—C23—O2 3.8 (2)
C4—C5—C6—C7 0.2 (4) C27—C22—C23—O2 −177.92 (15)
C5—C6—C7—C2 0.2 (3) O1—C22—C23—C24 −176.01 (16)
C3—C2—C7—C6 −0.6 (3) C27—C22—C23—C24 2.3 (3)
C1—C2—C7—C6 176.85 (17) O2—C23—C24—C25 178.99 (17)
O1—Sn1—C8—C9 13.55 (16) C22—C23—C24—C25 −1.2 (3)
C15—Sn1—C8—C9 −98.44 (16) C23—C24—C25—C26 −0.1 (3)
C1—Sn1—C8—C9 105.59 (16) C23—C24—C25—C28 179.63 (18)
O3i—Sn1—C8—C9 −178.30 (16) C24—C25—C26—C27 0.3 (3)
Sn1—C8—C9—C10 −67.3 (2) C28—C25—C26—C27 −179.43 (17)
Sn1—C8—C9—C14 113.34 (18) C25—C26—C27—C22 0.8 (3)
C14—C9—C10—C11 −0.9 (3) C25—C26—C27—N1 −178.67 (16)
C8—C9—C10—C11 179.72 (19) O1—C22—C27—C26 176.18 (17)
C9—C10—C11—C12 0.6 (3) C23—C22—C27—C26 −2.1 (3)
C10—C11—C12—C13 −0.2 (3) O1—C22—C27—N1 −4.3 (3)
C11—C12—C13—C14 0.0 (3) C23—C22—C27—N1 177.42 (15)
C12—C13—C14—C9 −0.3 (3) O5—N1—C27—C26 167.06 (18)
C10—C9—C14—C13 0.7 (3) O4—N1—C27—C26 −11.5 (2)
C8—C9—C14—C13 −179.89 (19) O5—N1—C27—C22 −12.4 (3)
O1—Sn1—C15—C16 88.15 (13) O4—N1—C27—C22 169.03 (17)
C1—Sn1—C15—C16 −2.56 (15) Sn1ii—O3—C28—C25 −177.02 (14)
C8—Sn1—C15—C16 −158.91 (12) C26—C25—C28—O3 175.07 (19)
O3i—Sn1—C15—C16 −79.02 (13) C24—C25—C28—O3 −4.7 (3)
Sn1—C15—C16—C17 −81.43 (19)
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Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2283).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  2. Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. James, B. D., Kivlinghon, L. M., Skelton, B. W. & White, A. H. (1998). Appl. Organomet. Chem. 12, 13–23.
  4. Poller, R. C. (1970). In The Chemistry of Organotin Compounds London: Academic Press.
  5. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016436/jh2283sup1.cif

e-67-0m710-sup1.cif (23.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016436/jh2283Isup2.hkl

e-67-0m710-Isup2.hkl (311.9KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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