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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Oct 11;64(Pt 11):m1390. doi: 10.1107/S1600536808032236

catena-Poly[[tribenzyl­tin(IV)]-μ-4-nitro­cinnamato-κ2 O:O′]

Pui Yee Thong a, Kong Mun Lo a, Seik Weng Ng a,*
PMCID: PMC2959618  PMID: 21580842

Abstract

The 4-nitro­cinnamate anion in the title compound, [Sn(C7H7)3(C9H6NO4)]n, bridges adjacent tribenzyl­tin cations into a helical chain running along the b axis. The Sn atoms in the two independent mol­ecules adopt distorted trans-C3SnO2 trigonal–bipyramidal geometries. The repeat distance of the polymeric chain is b/2.

Related literature

The trialkyltin derivatives of monocarboxylic acids generally adopt carboxyl­ate-bridged chain structures; see: Ng et al. (1989 ▶). For the trialkyl­tin/triaryl­tin derivatives of cinnamic acid and other substituted cinnamic acids, see: Ng & Kumar Das (1994 ▶); Siah et al. (1994 ▶); Willem et al. (1996 ▶). For the synthesis of tribenzyl­tin chloride, see: Sisido et al. (1961 ▶). For reviews of organotin carboxyl­ates, see: Tiekink (1991 ▶, 1994 ▶).graphic file with name e-64-m1390-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H7)3(C9H6NO4)]

  • M r = 584.22

  • Monoclinic, Inline graphic

  • a = 21.4850 (3) Å

  • b = 10.2134 (1) Å

  • c = 25.9562 (4) Å

  • β = 112.133 (1)°

  • V = 5276.0 (1) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 100 (2) K

  • 0.36 × 0.03 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.714, T max = 0.971

  • 48779 measured reflections

  • 12115 independent reflections

  • 9043 reflections with I > 2σ(I)

  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033

  • wR(F 2) = 0.091

  • S = 1.06

  • 12115 reflections

  • 565 parameters

  • 38 restraints

  • H-atom parameters constrained

  • Δρmax = 0.81 e Å−3

  • Δρmin = −0.80 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032236/tk2314sup1.cif

e-64-m1390-sup1.cif (37.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032236/tk2314Isup2.hkl

e-64-m1390-Isup2.hkl (592.3KB, hkl)

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

Acknowledgments

The authors thank the University of Malaya for funding this study (grant No. FS339/2008A).

supplementary crystallographic information

Comment

The polymeric structure found for tribenzyl(4-nitrocinnamato)tin(IV) conforms to expectation, Fig. 1 (Ng et al., 1989; Tiekink, 1991).

Experimental

Tribenzyltin chloride was synthesized from the direct reaction between tin powder and benzyl chloride in water (Sisido et al., 1961). The chloride was converted to tribenzyltin hydroxide by treatment with 10% sodium hydroxide in acetone. Tribenzyltin hydroxide (1.4 g, 0.3 mmol) and 4-nitrocinnamic acid (0.5 g, 0.3 mmol) were heated in ethanol (100 ml) for 1 h. Slow evaporation of the solvent yielded yellow prisms.

Refinement

The carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The nitro group in each independent molecule are disordered in their oxygen atoms. The nitrogen–oxygen distances for the unprimed and primed atoms were restrained to within 0.01 Å of each other. The C–NO2 fragment was restrained to be nearly planar, and the temperature factors of the primed atoms were set to those of the unprimed ones; the anisotropic displacement parameters of the disordered atoms were restrained to be nearly isotropic. The occupancy could not be refined, and was arbitrarily set at 0.5. All phenyl and phenylene rings were refined as rigid hexagons of 1.39 Å sides.

Figures

Fig. 1.

Fig. 1.

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70% Probability thermal ellipsoid plot (Barbour, 2001) of [(C6H5CH2)3SnO2CCH═CH—C6H4—NO2]∞. Hydrogen atoms are drawn as spheres of arbitrary radius. Only one orientation of the disordered nitro group is shown in each case.

Crystal data

[Sn(C7H7)3(C9H6NO4)] F(000) = 2368
Mr = 584.22 Dx = 1.471 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 9977 reflections
a = 21.4850 (3) Å θ = 2.4–28.3°
b = 10.2134 (1) Å µ = 1.00 mm−1
c = 25.9562 (4) Å T = 100 K
β = 112.133 (1)° Prism, pale yellow
V = 5276.0 (1) Å3 0.36 × 0.03 × 0.03 mm
Z = 8
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Data collection

Bruker SMART APEX diffractometer 12115 independent reflections
Radiation source: fine-focus sealed tube 9043 reflections with I > 2σ(I)
graphite Rint = 0.032
ω scans θmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −26→27
Tmin = 0.714, Tmax = 0.971 k = −13→13
48779 measured reflections l = −32→33
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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)] = 0.033 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091 H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0362P)2 + 8.7819P] where P = (Fo2 + 2Fc2)/3
12115 reflections (Δ/σ)max = 0.001
565 parameters Δρmax = 0.81 e Å−3
38 restraints Δρmin = −0.80 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
Sn1 0.740576 (10) 0.624465 (18) 0.773616 (8) 0.01626 (6)
Sn2 0.240598 (10) 0.527516 (18) 0.774258 (8) 0.01660 (6)
O1 0.72572 (11) 0.46521 (19) 0.82387 (9) 0.0208 (4)
O2 0.74811 (12) 0.3133 (2) 0.77179 (9) 0.0285 (5)
O3 0.5986 (4) −0.1699 (6) 1.0109 (5) 0.0358 (16) 0.50
O4 0.6223 (5) −0.0096 (19) 1.0718 (4) 0.063 (2) 0.50
O3' 0.6225 (4) −0.1780 (6) 1.0239 (5) 0.0358 (16) 0.50
O4' 0.5957 (5) −0.0086 (19) 1.0602 (4) 0.063 (2) 0.50
O5 0.22693 (12) 0.36739 (19) 0.82563 (9) 0.0239 (5)
O6 0.24714 (11) 0.2147 (2) 0.77260 (9) 0.0273 (5)
O7 0.1482 (10) −0.2711 (10) 1.0365 (13) 0.039 (2) 0.50
O8 0.0768 (8) −0.119 (3) 1.0434 (7) 0.047 (3) 0.50
O7' 0.1347 (10) −0.2814 (10) 1.0294 (13) 0.039 (2) 0.50
O8' 0.0890 (8) −0.125 (3) 1.0558 (7) 0.047 (3) 0.50
N1 0.61765 (12) −0.0592 (3) 1.02706 (11) 0.0367 (7)
N2 0.11891 (13) −0.1650 (3) 1.02647 (10) 0.0353 (7)
C1 0.71495 (17) 0.7671 (3) 0.82323 (13) 0.0229 (6)
H1A 0.7535 0.8275 0.8394 0.027*
H1B 0.6765 0.8193 0.7984 0.027*
C2 0.69693 (10) 0.7136 (2) 0.86959 (7) 0.0190 (6)
C3 0.63172 (9) 0.6732 (2) 0.85994 (8) 0.0312 (8)
H3 0.5977 0.6815 0.8239 0.037*
C4 0.61630 (11) 0.6204 (2) 0.90307 (12) 0.0484 (12)
H4 0.5717 0.5928 0.8965 0.058*
C5 0.66609 (15) 0.6082 (2) 0.95584 (10) 0.0544 (14)
H5 0.6555 0.5721 0.9853 0.065*
C6 0.73130 (13) 0.6487 (3) 0.96549 (7) 0.0502 (12)
H6 0.7653 0.6403 1.0016 0.060*
C7 0.74672 (8) 0.7014 (2) 0.92237 (8) 0.0320 (8)
H7 0.7913 0.7290 0.9290 0.038*
C8 0.84579 (15) 0.5814 (3) 0.79622 (13) 0.0225 (6)
H8A 0.8517 0.4871 0.7904 0.027*
H8B 0.8637 0.6322 0.7724 0.027*
C9 0.88404 (10) 0.61648 (18) 0.85682 (6) 0.0203 (6)
C10 0.88920 (10) 0.52659 (14) 0.89844 (8) 0.0227 (6)
H10 0.8693 0.4424 0.8890 0.027*
C11 0.92346 (10) 0.55980 (18) 0.95392 (7) 0.0257 (7)
H11 0.9270 0.4984 0.9824 0.031*
C12 0.95257 (10) 0.6829 (2) 0.96778 (6) 0.0278 (7)
H12 0.9760 0.7056 1.0057 0.033*
C13 0.94741 (10) 0.77282 (15) 0.92616 (8) 0.0266 (7)
H13 0.9673 0.8570 0.9356 0.032*
C14 0.91314 (10) 0.73960 (16) 0.87068 (7) 0.0219 (6)
H14 0.9096 0.8010 0.8422 0.026*
C15 0.66090 (15) 0.5625 (3) 0.69825 (13) 0.0215 (6)
H15A 0.6636 0.6116 0.6663 0.026*
H15B 0.6660 0.4681 0.6920 0.026*
C16 0.59325 (9) 0.5861 (2) 0.70202 (9) 0.0234 (7)
C17 0.56721 (10) 0.49508 (17) 0.72834 (9) 0.0270 (7)
H17 0.5912 0.4166 0.7428 0.032*
C18 0.50613 (11) 0.5189 (2) 0.73352 (10) 0.0362 (9)
H18 0.4883 0.4567 0.7515 0.043*
C19 0.47109 (9) 0.6337 (3) 0.71236 (11) 0.0442 (10)
H19 0.4293 0.6500 0.7159 0.053*
C20 0.49713 (11) 0.7247 (2) 0.68604 (11) 0.0467 (10)
H20 0.4732 0.8032 0.6716 0.056*
C21 0.55821 (11) 0.70092 (19) 0.68086 (10) 0.0352 (8)
H21 0.5760 0.7631 0.6629 0.042*
C22 0.73041 (15) 0.3466 (3) 0.81149 (12) 0.0193 (6)
C23 0.71423 (15) 0.2458 (3) 0.84523 (12) 0.0200 (6)
H23 0.7156 0.1561 0.8361 0.024*
C24 0.69782 (15) 0.2774 (3) 0.88809 (13) 0.0222 (6)
H24 0.6986 0.3679 0.8967 0.027*
C25 0.67857 (11) 0.18658 (16) 0.92365 (8) 0.0217 (6)
C26 0.66231 (12) 0.24047 (13) 0.96615 (9) 0.0273 (7)
H26 0.6651 0.3324 0.9721 0.033*
C27 0.64194 (12) 0.15980 (18) 1.00000 (8) 0.0300 (8)
H27 0.6308 0.1966 1.0290 0.036*
C28 0.63784 (12) 0.02523 (17) 0.99136 (8) 0.0260 (7)
C29 0.65410 (13) −0.02866 (13) 0.94886 (9) 0.0290 (8)
H29 0.6513 −0.1206 0.9430 0.035*
C30 0.67447 (12) 0.05201 (17) 0.91501 (8) 0.0279 (7)
H30 0.6856 0.0152 0.8860 0.034*
C31 0.34371 (15) 0.4752 (3) 0.78971 (13) 0.0234 (7)
H31A 0.3489 0.3789 0.7916 0.028*
H31B 0.3567 0.5082 0.7593 0.028*
C32 0.38785 (10) 0.5362 (2) 0.84441 (7) 0.0257 (7)
C33 0.39227 (11) 0.4797 (2) 0.89438 (9) 0.0348 (8)
H33 0.3704 0.3988 0.8943 0.042*
C34 0.42867 (12) 0.5415 (3) 0.94443 (7) 0.0456 (11)
H34 0.4317 0.5029 0.9786 0.055*
C35 0.46065 (12) 0.6599 (3) 0.94449 (8) 0.0482 (11)
H35 0.4855 0.7021 0.9787 0.058*
C36 0.45623 (11) 0.71638 (19) 0.89452 (11) 0.0425 (10)
H36 0.4781 0.7973 0.8946 0.051*
C37 0.41983 (11) 0.6546 (2) 0.84447 (8) 0.0327 (8)
H37 0.4168 0.6932 0.8103 0.039*
C38 0.23174 (16) 0.6679 (3) 0.83283 (13) 0.0207 (6)
H38A 0.2751 0.6712 0.8650 0.025*
H38B 0.2242 0.7552 0.8150 0.025*
C39 0.17661 (9) 0.6429 (2) 0.85455 (8) 0.0206 (6)
C40 0.18741 (8) 0.5606 (2) 0.89975 (8) 0.0258 (7)
H40 0.2299 0.5198 0.9176 0.031*
C41 0.13605 (11) 0.5380 (2) 0.91892 (8) 0.0325 (8)
H41 0.1434 0.4817 0.9498 0.039*
C42 0.07389 (9) 0.5977 (2) 0.89288 (9) 0.0349 (8)
H42 0.0388 0.5822 0.9060 0.042*
C43 0.06308 (8) 0.6800 (2) 0.84768 (9) 0.0376 (9)
H43 0.0206 0.7208 0.8299 0.045*
C44 0.11444 (10) 0.7026 (2) 0.82851 (8) 0.0293 (7)
H44 0.1071 0.7589 0.7976 0.035*
C45 0.15670 (16) 0.4719 (3) 0.70112 (14) 0.0245 (7)
H45A 0.1653 0.4998 0.6679 0.029*
H45B 0.1527 0.3753 0.7000 0.029*
C46 0.09086 (9) 0.5305 (2) 0.69842 (10) 0.0258 (7)
C47 0.05407 (12) 0.4697 (2) 0.72566 (10) 0.0370 (9)
H47 0.0697 0.3901 0.7452 0.044*
C48 −0.00562 (12) 0.5252 (3) 0.72425 (12) 0.0517 (12)
H48 −0.0308 0.4836 0.7429 0.062*
C49 −0.02853 (10) 0.6416 (3) 0.69561 (12) 0.0561 (13)
H49 −0.0693 0.6795 0.6946 0.067*
C50 0.00826 (13) 0.7024 (2) 0.66837 (11) 0.0506 (12)
H50 −0.0074 0.7820 0.6488 0.061*
C51 0.06795 (12) 0.6469 (2) 0.66978 (10) 0.0353 (8)
H51 0.0931 0.6885 0.6512 0.042*
C52 0.23218 (15) 0.2495 (3) 0.81304 (13) 0.0198 (6)
C53 0.21856 (16) 0.1483 (3) 0.84854 (13) 0.0211 (6)
H53 0.2298 0.0597 0.8450 0.025*
C54 0.19105 (17) 0.1782 (3) 0.88532 (13) 0.0254 (7)
H54 0.1828 0.2683 0.8893 0.030*
C55 0.17221 (12) 0.08569 (17) 0.92023 (9) 0.0255 (7)
C56 0.13401 (15) 0.13270 (16) 0.94915 (12) 0.0541 (13)
H56 0.1202 0.2217 0.9454 0.065*
C57 0.11599 (14) 0.0494 (2) 0.98357 (11) 0.0567 (14)
H57 0.0899 0.0816 1.0033 0.068*
C58 0.13617 (13) −0.08082 (19) 0.98908 (9) 0.0283 (7)
C59 0.17438 (12) −0.12784 (15) 0.96017 (9) 0.0288 (7)
H59 0.1882 −0.2169 0.9639 0.035*
C60 0.19240 (11) −0.04458 (19) 0.92574 (9) 0.0265 (7)
H60 0.2185 −0.0767 0.9060 0.032*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Sn1 0.02067 (11) 0.01290 (10) 0.01803 (10) −0.00047 (8) 0.01050 (8) −0.00080 (8)
Sn2 0.01892 (10) 0.01368 (10) 0.02153 (11) 0.00060 (8) 0.01256 (8) −0.00001 (8)
O1 0.0309 (12) 0.0125 (10) 0.0231 (11) −0.0006 (9) 0.0149 (10) −0.0016 (8)
O2 0.0385 (14) 0.0240 (12) 0.0296 (12) 0.0031 (10) 0.0203 (11) −0.0003 (10)
O3 0.046 (5) 0.0261 (15) 0.041 (4) −0.009 (2) 0.023 (4) 0.0018 (18)
O4 0.120 (7) 0.0448 (19) 0.049 (4) −0.019 (6) 0.060 (4) −0.008 (3)
O3' 0.046 (5) 0.0261 (15) 0.041 (4) −0.009 (2) 0.023 (4) 0.0018 (18)
O4' 0.120 (7) 0.0448 (19) 0.049 (4) −0.019 (6) 0.060 (4) −0.008 (3)
O5 0.0386 (13) 0.0129 (10) 0.0305 (12) 0.0013 (9) 0.0247 (11) 0.0013 (9)
O6 0.0357 (13) 0.0235 (12) 0.0315 (12) 0.0019 (10) 0.0228 (11) −0.0018 (10)
O7 0.035 (7) 0.039 (2) 0.037 (6) −0.014 (3) 0.008 (5) 0.013 (2)
O8 0.084 (5) 0.043 (3) 0.029 (6) −0.018 (4) 0.040 (5) −0.004 (6)
O7' 0.035 (7) 0.039 (2) 0.037 (6) −0.014 (3) 0.008 (5) 0.013 (2)
O8' 0.084 (5) 0.043 (3) 0.029 (6) −0.018 (4) 0.040 (5) −0.004 (6)
N1 0.063 (2) 0.0263 (16) 0.0308 (16) −0.0070 (15) 0.0295 (16) −0.0007 (13)
N2 0.0500 (19) 0.0320 (17) 0.0264 (15) −0.0184 (15) 0.0172 (14) −0.0017 (13)
C1 0.0378 (18) 0.0084 (13) 0.0267 (16) −0.0008 (12) 0.0169 (14) −0.0032 (12)
C2 0.0235 (15) 0.0129 (13) 0.0246 (15) 0.0027 (11) 0.0135 (13) −0.0024 (12)
C3 0.0278 (17) 0.0282 (17) 0.043 (2) −0.0029 (14) 0.0192 (16) −0.0153 (16)
C4 0.057 (3) 0.0265 (19) 0.091 (4) −0.0157 (18) 0.062 (3) −0.022 (2)
C5 0.108 (4) 0.0225 (19) 0.066 (3) 0.013 (2) 0.070 (3) 0.0097 (19)
C6 0.075 (3) 0.051 (3) 0.033 (2) 0.032 (2) 0.030 (2) 0.0167 (19)
C7 0.0285 (18) 0.042 (2) 0.0258 (17) 0.0099 (15) 0.0105 (14) −0.0001 (15)
C8 0.0256 (16) 0.0215 (15) 0.0253 (16) 0.0038 (13) 0.0152 (13) 0.0028 (13)
C9 0.0186 (15) 0.0209 (15) 0.0253 (16) 0.0035 (12) 0.0127 (13) 0.0033 (12)
C10 0.0217 (15) 0.0198 (15) 0.0293 (17) 0.0035 (12) 0.0127 (13) 0.0056 (13)
C11 0.0248 (16) 0.0286 (17) 0.0275 (17) 0.0080 (14) 0.0140 (14) 0.0099 (14)
C12 0.0263 (17) 0.0344 (18) 0.0230 (16) 0.0053 (14) 0.0098 (14) −0.0028 (14)
C13 0.0250 (16) 0.0219 (16) 0.0337 (18) 0.0021 (13) 0.0119 (14) −0.0034 (14)
C14 0.0222 (15) 0.0189 (15) 0.0291 (16) 0.0037 (12) 0.0146 (13) 0.0057 (12)
C15 0.0237 (16) 0.0210 (15) 0.0223 (15) −0.0019 (12) 0.0115 (13) −0.0034 (12)
C16 0.0212 (16) 0.0246 (16) 0.0233 (16) −0.0016 (13) 0.0071 (13) −0.0064 (13)
C17 0.0287 (17) 0.0275 (17) 0.0257 (17) −0.0075 (14) 0.0112 (14) −0.0077 (14)
C18 0.0291 (19) 0.049 (2) 0.0323 (19) −0.0132 (17) 0.0134 (16) −0.0112 (17)
C19 0.0226 (18) 0.069 (3) 0.043 (2) −0.0029 (18) 0.0144 (17) −0.010 (2)
C20 0.031 (2) 0.054 (3) 0.054 (3) 0.0162 (19) 0.0138 (19) 0.002 (2)
C21 0.0315 (19) 0.034 (2) 0.040 (2) 0.0057 (15) 0.0131 (16) 0.0026 (16)
C22 0.0207 (15) 0.0162 (14) 0.0223 (15) 0.0007 (12) 0.0094 (12) −0.0022 (12)
C23 0.0235 (15) 0.0118 (14) 0.0251 (15) −0.0007 (11) 0.0097 (13) 0.0009 (11)
C24 0.0281 (16) 0.0139 (14) 0.0275 (16) −0.0021 (12) 0.0137 (13) −0.0006 (12)
C25 0.0275 (16) 0.0177 (14) 0.0230 (15) −0.0006 (12) 0.0130 (13) 0.0005 (12)
C26 0.041 (2) 0.0175 (15) 0.0290 (17) 0.0022 (14) 0.0197 (15) −0.0006 (13)
C27 0.046 (2) 0.0271 (17) 0.0273 (17) 0.0006 (15) 0.0255 (16) −0.0036 (14)
C28 0.0375 (19) 0.0219 (16) 0.0228 (16) −0.0024 (14) 0.0162 (15) 0.0008 (13)
C29 0.048 (2) 0.0177 (16) 0.0295 (18) −0.0028 (14) 0.0237 (17) −0.0017 (13)
C30 0.044 (2) 0.0207 (15) 0.0280 (17) −0.0046 (14) 0.0242 (16) −0.0037 (13)
C31 0.0234 (16) 0.0205 (15) 0.0306 (17) 0.0049 (12) 0.0152 (14) 0.0003 (13)
C32 0.0178 (15) 0.0264 (17) 0.0331 (18) 0.0069 (13) 0.0098 (14) 0.0017 (14)
C33 0.0247 (18) 0.048 (2) 0.0314 (19) 0.0064 (16) 0.0106 (15) 0.0059 (17)
C34 0.028 (2) 0.076 (3) 0.031 (2) 0.010 (2) 0.0098 (16) 0.003 (2)
C35 0.0255 (19) 0.068 (3) 0.043 (2) 0.008 (2) 0.0039 (17) −0.020 (2)
C36 0.0274 (19) 0.035 (2) 0.058 (3) 0.0038 (16) 0.0083 (18) −0.0115 (19)
C37 0.0241 (17) 0.0282 (18) 0.044 (2) 0.0077 (14) 0.0114 (16) 0.0036 (16)
C38 0.0283 (16) 0.0136 (14) 0.0254 (16) 0.0005 (12) 0.0160 (13) −0.0013 (12)
C39 0.0265 (16) 0.0176 (15) 0.0214 (15) 0.0026 (12) 0.0133 (13) −0.0015 (12)
C40 0.0308 (17) 0.0246 (16) 0.0266 (17) 0.0092 (14) 0.0161 (14) 0.0039 (13)
C41 0.050 (2) 0.0233 (17) 0.0348 (19) 0.0058 (15) 0.0287 (18) 0.0055 (14)
C42 0.034 (2) 0.042 (2) 0.041 (2) −0.0001 (16) 0.0278 (17) −0.0043 (17)
C43 0.0273 (18) 0.056 (2) 0.0338 (19) 0.0129 (17) 0.0167 (16) 0.0014 (18)
C44 0.0311 (18) 0.0361 (19) 0.0250 (17) 0.0106 (15) 0.0155 (14) 0.0043 (14)
C45 0.0260 (16) 0.0216 (16) 0.0281 (17) −0.0034 (13) 0.0127 (14) −0.0052 (13)
C46 0.0207 (16) 0.0269 (17) 0.0284 (17) −0.0036 (13) 0.0076 (14) −0.0088 (13)
C47 0.033 (2) 0.034 (2) 0.051 (2) −0.0086 (16) 0.0228 (18) −0.0098 (17)
C48 0.029 (2) 0.066 (3) 0.066 (3) −0.012 (2) 0.024 (2) −0.022 (2)
C49 0.024 (2) 0.079 (3) 0.056 (3) 0.012 (2) 0.0045 (19) −0.026 (3)
C50 0.043 (2) 0.047 (3) 0.043 (2) 0.019 (2) −0.0054 (19) −0.011 (2)
C51 0.033 (2) 0.033 (2) 0.0335 (19) 0.0032 (16) 0.0055 (16) −0.0051 (16)
C52 0.0217 (15) 0.0124 (14) 0.0301 (16) −0.0002 (11) 0.0151 (13) 0.0011 (12)
C53 0.0278 (16) 0.0114 (13) 0.0265 (16) −0.0008 (12) 0.0130 (13) 0.0007 (12)
C54 0.0351 (18) 0.0152 (14) 0.0302 (17) −0.0009 (13) 0.0173 (15) −0.0025 (13)
C55 0.0369 (19) 0.0210 (15) 0.0247 (16) −0.0049 (14) 0.0185 (15) −0.0006 (13)
C56 0.106 (4) 0.0200 (18) 0.075 (3) 0.008 (2) 0.078 (3) 0.0062 (19)
C57 0.110 (4) 0.027 (2) 0.073 (3) 0.003 (2) 0.080 (3) 0.002 (2)
C58 0.041 (2) 0.0245 (17) 0.0223 (16) −0.0130 (15) 0.0158 (15) −0.0032 (13)
C59 0.0326 (18) 0.0236 (16) 0.0310 (18) −0.0021 (14) 0.0129 (15) 0.0034 (14)
C60 0.0326 (18) 0.0217 (16) 0.0297 (17) −0.0009 (13) 0.0169 (15) 0.0009 (13)
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Geometric parameters (Å, °)

Sn1—C1 2.149 (3) C23—H23 0.9500
Sn1—C15 2.153 (3) C24—C25 1.473 (3)
Sn1—C8 2.156 (3) C24—H24 0.9500
Sn1—O1 2.182 (2) C25—C26 1.3900
Sn1—O2i 2.320 (2) C25—C30 1.3900
Sn2—C45 2.144 (3) C26—C27 1.3900
Sn2—C38 2.149 (3) C26—H26 0.9500
Sn2—C31 2.164 (3) C27—C28 1.3900
Sn2—O5 2.199 (2) C27—H27 0.9500
Sn2—O6ii 2.334 (2) C28—C29 1.3900
O1—C22 1.267 (3) C29—C30 1.3900
O2—C22 1.272 (3) C29—H29 0.9500
O2—Sn1iii 2.320 (2) C30—H30 0.9500
O3—N1 1.222 (6) C31—C32 1.513 (4)
O4—N1 1.235 (7) C31—H31A 0.9900
O3'—N1 1.223 (6) C31—H31B 0.9900
O4'—N1 1.238 (7) C32—C33 1.3900
O5—C52 1.264 (3) C32—C37 1.3900
O6—C52 1.259 (3) C33—C34 1.3900
O6—Sn2iv 2.334 (2) C33—H33 0.9500
O7—N2 1.231 (7) C34—C35 1.3900
O8—N2 1.240 (7) C34—H34 0.9500
O7'—N2 1.230 (7) C35—C36 1.3900
O8'—N2 1.235 (7) C35—H35 0.9500
N1—C28 1.447 (3) C36—C37 1.3900
N2—C58 1.446 (3) C36—H36 0.9500
C1—C2 1.499 (3) C37—H37 0.9500
C1—H1A 0.9900 C38—C39 1.513 (3)
C1—H1B 0.9900 C38—H38A 0.9900
C2—C3 1.3900 C38—H38B 0.9900
C2—C7 1.3900 C39—C40 1.3900
C3—C4 1.3900 C39—C44 1.3900
C3—H3 0.9500 C40—C41 1.3900
C4—C5 1.3900 C40—H40 0.9500
C4—H4 0.9500 C41—C42 1.3900
C5—C6 1.3900 C41—H41 0.9500
C5—H5 0.9500 C42—C43 1.3900
C6—C7 1.3900 C42—H42 0.9500
C6—H6 0.9500 C43—C44 1.3900
C7—H7 0.9500 C43—H43 0.9500
C8—C9 1.518 (3) C44—H44 0.9500
C8—H8A 0.9900 C45—C46 1.513 (3)
C8—H8B 0.9900 C45—H45A 0.9900
C9—C10 1.3900 C45—H45B 0.9900
C9—C14 1.3900 C46—C47 1.3900
C10—C11 1.3900 C46—C51 1.3900
C10—H10 0.9500 C47—C48 1.3900
C11—C12 1.3900 C47—H47 0.9500
C11—H11 0.9500 C48—C49 1.3900
C12—C13 1.3900 C48—H48 0.9500
C12—H12 0.9500 C49—C50 1.3900
C13—C14 1.3900 C49—H49 0.9500
C13—H13 0.9500 C50—C51 1.3900
C14—H14 0.9500 C50—H50 0.9500
C15—C16 1.512 (3) C51—H51 0.9500
C15—H15A 0.9900 C52—C53 1.485 (4)
C15—H15B 0.9900 C53—C54 1.334 (4)
C16—C17 1.3900 C53—H53 0.9500
C16—C21 1.3900 C54—C55 1.468 (3)
C17—C18 1.3900 C54—H54 0.9500
C17—H17 0.9500 C55—C56 1.3900
C18—C19 1.3900 C55—C60 1.3900
C18—H18 0.9500 C56—C57 1.3900
C19—C20 1.3900 C56—H56 0.9500
C19—H19 0.9500 C57—C58 1.3900
C20—C21 1.3900 C57—H57 0.9500
C20—H20 0.9500 C58—C59 1.3900
C21—H21 0.9500 C59—C60 1.3900
C22—C23 1.476 (4) C59—H59 0.9500
C23—C24 1.327 (4) C60—H60 0.9500
C1—Sn1—C15 116.64 (12) C26—C25—C30 120.0
C1—Sn1—C8 117.02 (13) C26—C25—C24 117.50 (17)
C15—Sn1—C8 125.49 (12) C30—C25—C24 122.48 (17)
C1—Sn1—O1 91.07 (9) C25—C26—C27 120.0
C15—Sn1—O1 94.51 (10) C25—C26—H26 120.0
C8—Sn1—O1 93.42 (10) C27—C26—H26 120.0
C1—Sn1—O2i 80.82 (10) C26—C27—C28 120.0
C15—Sn1—O2i 89.00 (10) C26—C27—H27 120.0
C8—Sn1—O2i 90.47 (10) C28—C27—H27 120.0
O1—Sn1—O2i 171.89 (8) C29—C28—C27 120.0
C45—Sn2—C38 122.28 (12) C29—C28—N1 119.86 (17)
C45—Sn2—C31 123.99 (12) C27—C28—N1 120.13 (17)
C38—Sn2—C31 112.99 (12) C28—C29—C30 120.0
C45—Sn2—O5 94.59 (11) C28—C29—H29 120.0
C38—Sn2—O5 89.97 (9) C30—C29—H29 120.0
C31—Sn2—O5 93.75 (10) C29—C30—C25 120.0
C45—Sn2—O6ii 88.74 (10) C29—C30—H30 120.0
C38—Sn2—O6ii 83.09 (10) C25—C30—H30 120.0
C31—Sn2—O6ii 89.43 (10) C32—C31—Sn2 107.96 (18)
O5—Sn2—O6ii 173.04 (8) C32—C31—H31A 110.1
C22—O1—Sn1 121.17 (19) Sn2—C31—H31A 110.1
C22—O2—Sn1iii 139.0 (2) C32—C31—H31B 110.1
C52—O5—Sn2 120.44 (19) Sn2—C31—H31B 110.1
C52—O6—Sn2iv 141.3 (2) H31A—C31—H31B 108.4
O3—N1—O4 126.9 (12) C33—C32—C37 120.0
O3'—N1—O4' 121.7 (12) C33—C32—C31 120.21 (19)
O3—N1—C28 118.3 (7) C37—C32—C31 119.60 (18)
O3'—N1—C28 119.6 (7) C32—C33—C34 120.0
O4—N1—C28 114.8 (10) C32—C33—H33 120.0
O4'—N1—C28 118.7 (11) C34—C33—H33 120.0
O7'—N2—O8' 118 (3) C33—C34—C35 120.0
O7—N2—O8 130 (2) C33—C34—H34 120.0
O7'—N2—C58 118.8 (18) C35—C34—H34 120.0
O7—N2—C58 115.1 (18) C36—C35—C34 120.0
O8'—N2—C58 122.7 (16) C36—C35—H35 120.0
O8—N2—C58 114.7 (15) C34—C35—H35 120.0
C2—C1—Sn1 115.87 (18) C35—C36—C37 120.0
C2—C1—H1A 108.3 C35—C36—H36 120.0
Sn1—C1—H1A 108.3 C37—C36—H36 120.0
C2—C1—H1B 108.3 C36—C37—C32 120.0
Sn1—C1—H1B 108.3 C36—C37—H37 120.0
H1A—C1—H1B 107.4 C32—C37—H37 120.0
C3—C2—C7 120.0 C39—C38—Sn2 116.21 (18)
C3—C2—C1 120.75 (19) C39—C38—H38A 108.2
C7—C2—C1 119.23 (19) Sn2—C38—H38A 108.2
C2—C3—C4 120.0 C39—C38—H38B 108.2
C2—C3—H3 120.0 Sn2—C38—H38B 108.2
C4—C3—H3 120.0 H38A—C38—H38B 107.4
C5—C4—C3 120.0 C40—C39—C44 120.0
C5—C4—H4 120.0 C40—C39—C38 120.74 (17)
C3—C4—H4 120.0 C44—C39—C38 119.26 (17)
C4—C5—C6 120.0 C39—C40—C41 120.0
C4—C5—H5 120.0 C39—C40—H40 120.0
C6—C5—H5 120.0 C41—C40—H40 120.0
C5—C6—C7 120.0 C42—C41—C40 120.0
C5—C6—H6 120.0 C42—C41—H41 120.0
C7—C6—H6 120.0 C40—C41—H41 120.0
C6—C7—C2 120.0 C41—C42—C43 120.0
C6—C7—H7 120.0 C41—C42—H42 120.0
C2—C7—H7 120.0 C43—C42—H42 120.0
C9—C8—Sn1 109.68 (17) C44—C43—C42 120.0
C9—C8—H8A 109.7 C44—C43—H43 120.0
Sn1—C8—H8A 109.7 C42—C43—H43 120.0
C9—C8—H8B 109.7 C43—C44—C39 120.0
Sn1—C8—H8B 109.7 C43—C44—H44 120.0
H8A—C8—H8B 108.2 C39—C44—H44 120.0
C10—C9—C14 120.0 C46—C45—Sn2 113.29 (19)
C10—C9—C8 120.19 (17) C46—C45—H45A 108.9
C14—C9—C8 119.81 (17) Sn2—C45—H45A 108.9
C9—C10—C11 120.0 C46—C45—H45B 108.9
C9—C10—H10 120.0 Sn2—C45—H45B 108.9
C11—C10—H10 120.0 H45A—C45—H45B 107.7
C12—C11—C10 120.0 C47—C46—C51 120.0
C12—C11—H11 120.0 C47—C46—C45 120.02 (19)
C10—C11—H11 120.0 C51—C46—C45 119.97 (19)
C11—C12—C13 120.0 C46—C47—C48 120.0
C11—C12—H12 120.0 C46—C47—H47 120.0
C13—C12—H12 120.0 C48—C47—H47 120.0
C14—C13—C12 120.0 C47—C48—C49 120.0
C14—C13—H13 120.0 C47—C48—H48 120.0
C12—C13—H13 120.0 C49—C48—H48 120.0
C13—C14—C9 120.0 C50—C49—C48 120.0
C13—C14—H14 120.0 C50—C49—H49 120.0
C9—C14—H14 120.0 C48—C49—H49 120.0
C16—C15—Sn1 110.42 (18) C49—C50—C51 120.0
C16—C15—H15A 109.6 C49—C50—H50 120.0
Sn1—C15—H15A 109.6 C51—C50—H50 120.0
C16—C15—H15B 109.6 C50—C51—C46 120.0
Sn1—C15—H15B 109.6 C50—C51—H51 120.0
H15A—C15—H15B 108.1 C46—C51—H51 120.0
C17—C16—C21 120.0 O6—C52—O5 124.0 (3)
C17—C16—C15 119.98 (18) O6—C52—C53 119.5 (3)
C21—C16—C15 119.98 (18) O5—C52—C53 116.4 (3)
C18—C17—C16 120.0 C54—C53—C52 121.9 (3)
C18—C17—H17 120.0 C54—C53—H53 119.0
C16—C17—H17 120.0 C52—C53—H53 119.0
C17—C18—C19 120.0 C53—C54—C55 126.4 (3)
C17—C18—H18 120.0 C53—C54—H54 116.8
C19—C18—H18 120.0 C55—C54—H54 116.8
C20—C19—C18 120.0 C56—C55—C60 120.0
C20—C19—H19 120.0 C56—C55—C54 117.85 (18)
C18—C19—H19 120.0 C60—C55—C54 122.14 (18)
C19—C20—C21 120.0 C57—C56—C55 120.0
C19—C20—H20 120.0 C57—C56—H56 120.0
C21—C20—H20 120.0 C55—C56—H56 120.0
C20—C21—C16 120.0 C56—C57—C58 120.0
C20—C21—H21 120.0 C56—C57—H57 120.0
C16—C21—H21 120.0 C58—C57—H57 120.0
O1—C22—O2 122.5 (3) C57—C58—C59 120.0
O1—C22—C23 117.2 (3) C57—C58—N2 119.3 (2)
O2—C22—C23 120.2 (3) C59—C58—N2 120.7 (2)
C24—C23—C22 121.6 (3) C60—C59—C58 120.0
C24—C23—H23 119.2 C60—C59—H59 120.0
C22—C23—H23 119.2 C58—C59—H59 120.0
C23—C24—C25 126.7 (3) C59—C60—C55 120.0
C23—C24—H24 116.6 C59—C60—H60 120.0
C25—C24—H24 116.6 C55—C60—H60 120.0
C1—Sn1—O1—C22 175.8 (2) C28—C29—C30—C25 0.0
C15—Sn1—O1—C22 58.9 (2) C26—C25—C30—C29 0.0
C8—Sn1—O1—C22 −67.1 (2) C24—C25—C30—C29 −178.1 (2)
C45—Sn2—O5—C52 62.7 (3) C45—Sn2—C31—C32 178.15 (17)
C38—Sn2—O5—C52 −174.9 (3) C38—Sn2—C31—C32 7.8 (2)
C31—Sn2—O5—C52 −61.9 (3) O5—Sn2—C31—C32 −83.74 (19)
C15—Sn1—C1—C2 94.9 (2) O6ii—Sn2—C31—C32 90.06 (18)
C8—Sn1—C1—C2 −95.0 (2) Sn2—C31—C32—C33 77.7 (2)
O1—Sn1—C1—C2 −0.6 (2) Sn2—C31—C32—C37 −97.25 (18)
O2i—Sn1—C1—C2 179.2 (2) C37—C32—C33—C34 0.0
Sn1—C1—C2—C3 −85.2 (2) C31—C32—C33—C34 −175.0 (2)
Sn1—C1—C2—C7 93.0 (2) C32—C33—C34—C35 0.0
C7—C2—C3—C4 0.0 C33—C34—C35—C36 0.0
C1—C2—C3—C4 178.2 (2) C34—C35—C36—C37 0.0
C2—C3—C4—C5 0.0 C35—C36—C37—C32 0.0
C3—C4—C5—C6 0.0 C33—C32—C37—C36 0.0
C4—C5—C6—C7 0.0 C31—C32—C37—C36 175.0 (2)
C5—C6—C7—C2 0.0 C45—Sn2—C38—C39 52.1 (2)
C3—C2—C7—C6 0.0 C31—Sn2—C38—C39 −137.34 (19)
C1—C2—C7—C6 −178.2 (2) O5—Sn2—C38—C39 −43.3 (2)
C1—Sn1—C8—C9 22.8 (2) O6ii—Sn2—C38—C39 136.2 (2)
C15—Sn1—C8—C9 −168.14 (16) Sn2—C38—C39—C40 85.3 (2)
O1—Sn1—C8—C9 −70.14 (18) Sn2—C38—C39—C44 −94.2 (2)
O2i—Sn1—C8—C9 102.75 (18) C44—C39—C40—C41 0.0
Sn1—C8—C9—C10 86.16 (19) C38—C39—C40—C41 −179.5 (2)
Sn1—C8—C9—C14 −92.93 (18) C39—C40—C41—C42 0.0
C14—C9—C10—C11 0.0 C40—C41—C42—C43 0.0
C8—C9—C10—C11 −179.1 (2) C41—C42—C43—C44 0.0
C9—C10—C11—C12 0.0 C42—C43—C44—C39 0.0
C10—C11—C12—C13 0.0 C40—C39—C44—C43 0.0
C11—C12—C13—C14 0.0 C38—C39—C44—C43 179.5 (2)
C12—C13—C14—C9 0.0 C38—Sn2—C45—C46 −5.7 (3)
C10—C9—C14—C13 0.0 C31—Sn2—C45—C46 −175.18 (18)
C8—C9—C14—C13 179.1 (2) O5—Sn2—C45—C46 87.2 (2)
C1—Sn1—C15—C16 −22.7 (2) O6ii—Sn2—C45—C46 −86.7 (2)
C8—Sn1—C15—C16 168.22 (17) Sn2—C45—C46—C47 −84.2 (2)
O1—Sn1—C15—C16 70.77 (19) Sn2—C45—C46—C51 94.3 (2)
O2i—Sn1—C15—C16 −101.91 (19) C51—C46—C47—C48 0.0
Sn1—C15—C16—C17 −83.3 (2) C45—C46—C47—C48 178.5 (2)
Sn1—C15—C16—C21 94.47 (19) C46—C47—C48—C49 0.0
C21—C16—C17—C18 0.0 C47—C48—C49—C50 0.0
C15—C16—C17—C18 177.8 (2) C48—C49—C50—C51 0.0
C16—C17—C18—C19 0.0 C49—C50—C51—C46 0.0
C17—C18—C19—C20 0.0 C47—C46—C51—C50 0.0
C18—C19—C20—C21 0.0 C45—C46—C51—C50 −178.5 (2)
C19—C20—C21—C16 0.0 Sn2iv—O6—C52—O5 −176.0 (2)
C17—C16—C21—C20 0.0 Sn2iv—O6—C52—C53 3.1 (5)
C15—C16—C21—C20 −177.8 (2) Sn2—O5—C52—O6 2.2 (4)
Sn1—O1—C22—O2 4.7 (4) Sn2—O5—C52—C53 −176.9 (2)
Sn1—O1—C22—C23 −175.23 (19) O6—C52—C53—C54 −167.7 (3)
Sn1iii—O2—C22—O1 −175.1 (2) O5—C52—C53—C54 11.4 (5)
Sn1iii—O2—C22—C23 4.8 (5) C52—C53—C54—C55 176.5 (3)
O1—C22—C23—C24 −2.4 (4) C53—C54—C55—C56 −169.4 (3)
O2—C22—C23—C24 177.7 (3) C53—C54—C55—C60 11.8 (5)
C22—C23—C24—C25 177.8 (3) C60—C55—C56—C57 0.0
C23—C24—C25—C26 −179.2 (3) C54—C55—C56—C57 −178.8 (2)
C23—C24—C25—C30 −1.0 (4) C55—C56—C57—C58 0.0
C30—C25—C26—C27 0.0 C56—C57—C58—C59 0.0
C24—C25—C26—C27 178.2 (2) C56—C57—C58—N2 178.0 (2)
C25—C26—C27—C28 0.0 O7'—N2—C58—C57 177.1 (10)
C26—C27—C28—C29 0.0 O7—N2—C58—C57 −167.7 (10)
C26—C27—C28—N1 179.1 (2) O8'—N2—C58—C57 −3.0 (10)
O3—N1—C28—C29 −18.7 (4) O8—N2—C58—C57 12.3 (10)
O3'—N1—C28—C29 8.5 (4) O7'—N2—C58—C59 −4.9 (10)
O4—N1—C28—C29 160.8 (5) O7—N2—C58—C59 10.2 (10)
O4'—N1—C28—C29 −171.4 (4) O8'—N2—C58—C59 175.0 (10)
O3—N1—C28—C27 162.2 (4) O8—N2—C58—C59 −169.8 (10)
O3'—N1—C28—C27 −170.6 (4) C57—C58—C59—C60 0.0
O4—N1—C28—C27 −18.3 (5) N2—C58—C59—C60 −177.9 (2)
O4'—N1—C28—C27 9.5 (4) C58—C59—C60—C55 0.0
C27—C28—C29—C30 0.0 C56—C55—C60—C59 0.0
N1—C28—C29—C30 −179.1 (2) C54—C55—C60—C59 178.7 (3)
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Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2314).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  2. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Ng, S. W., Chen, W. & Kumar Das, V. G. (1989). J. Organomet. Chem.345, 59–64.
  4. Ng, S. W. & Kumar Das, V. G. (1994). Z. Kristallogr.209, 742–743.
  5. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Siah, L. F., Ng, S. W., Gielen, M. & Kumar Das, V. G. (1994). Malays. J. Sci. Sect. B, 15, 13–22.
  8. Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc.83, 538–541.
  9. Tiekink, E. R. T. (1991). Appl. Organomet. Chem.5, 1–23.
  10. Tiekink, E. R. T. (1994). Trends Organomet. Chem.1, 71–116.
  11. Westrip, S. P. (2008). publCIF In preparation.
  12. Willem, R., Bouhdid, A., Biesemans, M., Martins, J. C., de Vos, D., Tiekink, E. R. T. & Gielen, M. (1996). J. Organomet. Chem.514, 203–212.

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/S1600536808032236/tk2314sup1.cif

e-64-m1390-sup1.cif (37.4KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032236/tk2314Isup2.hkl

e-64-m1390-Isup2.hkl (592.3KB, 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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