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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Jul 4;65(Pt 8):m862. doi: 10.1107/S1600536809024477

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

See Mun Lee a, Kong Mun Lo a, Hapipah Mohd Ali a, Seik Weng Ng a,*
PMCID: PMC2977471  PMID: 21583330

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 ▶); Samanta et al. (2007 ▶).graphic file with name e-65-0m862-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C18H11BrN2O3)]

  • M r = 616.11

  • Triclinic, Inline graphic

  • 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 ▶) 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 ▶); 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, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024477/xu2544sup1.cif

e-65-0m862-sup1.cif (26.2KB, cif)

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

e-65-0m862-Isup2.hkl (281KB, 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.

Fig. 1.

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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 = 616.11 F(000) = 616
Triclinic, P1 Dx = 1.629 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 10.1626 (2) Å Cell parameters from 5075 reflections
b = 12.2534 (2) Å θ = 2.5–29.6°
c = 12.5583 (2) Å µ = 2.64 mm−1
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
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Data collection

Bruker SMART APEX diffractometer 5740 independent reflections
Radiation source: fine-focus sealed tube 4886 reflections with I > 2σ(I)
graphite Rint = 0.020
ω scans θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −13→13
Tmin = 0.515, Tmax = 0.621 k = −15→15
12053 measured reflections l = −16→16
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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)] = 0.025 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060 H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0287P)2 + 0.3063P] where P = (Fo2 + 2Fc2)/3
5740 reflections (Δ/σ)max = 0.001
342 parameters Δρmax = 0.53 e Å−3
47 restraints Δρmin = −0.59 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 0.828380 (16) 0.685444 (15) 0.242560 (14) 0.02643 (5)
Br1 0.66105 (3) 1.14077 (3) 0.54233 (3) 0.04563 (8)
N1 0.62849 (19) 0.86055 (18) 0.22108 (16) 0.0253 (4)
N2 0.51208 (19) 0.88674 (18) 0.15093 (16) 0.0269 (4)
O1 0.91148 (17) 0.75767 (16) 0.32829 (17) 0.0373 (4)
O2 0.67073 (17) 0.70268 (15) 0.12755 (14) 0.0312 (4)
O3 0.24653 (18) 1.01189 (17) 0.04941 (17) 0.0377 (4)
H3 0.316 (2) 0.997 (3) 0.091 (2) 0.043 (8)*
C1 0.9977 (13) 0.6790 (7) 0.1322 (11) 0.033 (2) 0.604 (8)
H1A 0.9610 0.7589 0.0518 0.040* 0.604 (8)
H1B 1.0748 0.6859 0.1674 0.040* 0.604 (8)
C2 1.0651 (6) 0.5515 (4) 0.1148 (4) 0.0393 (14) 0.604 (8)
H2A 0.9899 0.5474 0.0747 0.047* 0.604 (8)
H2B 1.1428 0.5585 0.0605 0.047* 0.604 (8)
C3 1.1279 (6) 0.4224 (5) 0.2312 (5) 0.0407 (14) 0.604 (8)
H3A 1.0489 0.4069 0.2811 0.049* 0.604 (8)
H3B 1.1940 0.4299 0.2774 0.049* 0.604 (8)
C4 1.2132 (13) 0.3006 (7) 0.2037 (10) 0.053 (3) 0.604 (8)
H4A 1.2446 0.2161 0.2796 0.079* 0.604 (8)
H4B 1.2983 0.3108 0.1628 0.079* 0.604 (8)
H4C 1.1501 0.2987 0.1513 0.079* 0.604 (8)
C1' 0.9820 (16) 0.6826 (9) 0.1057 (16) 0.027 (3) 0.396 (8)
H1C 0.9347 0.6928 0.0347 0.032* 0.396 (8)
H1D 1.0088 0.7599 0.0786 0.032* 0.396 (8)
C2' 1.1199 (7) 0.5504 (6) 0.1557 (8) 0.037 (2) 0.396 (8)
H2C 1.1921 0.5585 0.0961 0.044* 0.396 (8)
H2D 1.1619 0.5366 0.2307 0.044* 0.396 (8)
C3' 1.0915 (9) 0.4283 (7) 0.1826 (10) 0.047 (2) 0.396 (8)
H3C 1.0529 0.4391 0.1076 0.056* 0.396 (8)
H3D 1.0187 0.4194 0.2416 0.056* 0.396 (8)
C4' 1.2367 (15) 0.2992 (9) 0.2356 (14) 0.045 (3) 0.396 (8)
H4D 1.2299 0.2276 0.2245 0.068* 0.396 (8)
H4E 1.2546 0.2687 0.3221 0.068* 0.396 (8)
H4F 1.3167 0.3204 0.1936 0.068* 0.396 (8)
C5 0.8159 (2) 0.5186 (2) 0.4004 (2) 0.0270 (5)
H5A 0.7944 0.4611 0.3760 0.032*
H5B 0.9116 0.4638 0.4490 0.032*
C6 0.7010 (2) 0.5593 (2) 0.4793 (2) 0.0284 (5)
H6A 0.7220 0.6169 0.5039 0.034*
H6B 0.6049 0.6132 0.4315 0.034*
C7 0.6958 (3) 0.4372 (2) 0.5921 (2) 0.0334 (5)
H7A 0.6758 0.3792 0.5673 0.040*
H7B 0.7918 0.3837 0.6400 0.040*
C8 0.5807 (3) 0.4764 (3) 0.6711 (2) 0.0438 (6)
H8A 0.5856 0.3950 0.7443 0.066*
H8B 0.4845 0.5231 0.6263 0.066*
H8C 0.5978 0.5365 0.6935 0.066*
C9 0.8505 (2) 0.8415 (2) 0.3749 (2) 0.0300 (5)
C10 0.9369 (3) 0.8446 (2) 0.4528 (2) 0.0366 (6)
H10 1.0369 0.7856 0.4712 0.044*
C11 0.8800 (3) 0.9309 (2) 0.5027 (2) 0.0352 (6)
H11 0.9402 0.9297 0.5565 0.042*
C12 0.7347 (3) 1.0201 (2) 0.4748 (2) 0.0323 (5)
C13 0.6465 (2) 1.0216 (2) 0.3985 (2) 0.0298 (5)
H13 0.5475 1.0835 0.3794 0.036*
C14 0.7019 (2) 0.9314 (2) 0.3481 (2) 0.0268 (5)
C15 0.6026 (2) 0.9392 (2) 0.2698 (2) 0.0265 (5)
H15 0.5080 1.0093 0.2516 0.032*
C16 0.5445 (2) 0.8009 (2) 0.10719 (19) 0.0265 (5)
C17 0.4293 (2) 0.8171 (2) 0.03210 (19) 0.0267 (5)
C18 0.4605 (2) 0.7287 (2) −0.01503 (19) 0.0265 (5)
H18 0.5566 0.6618 −0.0006 0.032*
C19 0.3555 (3) 0.7338 (2) −0.08373 (19) 0.0290 (5)
C20 0.3883 (3) 0.6414 (2) −0.1309 (2) 0.0339 (5)
H20 0.4847 0.5757 −0.1188 0.041*
C21 0.2825 (3) 0.6461 (3) −0.1935 (2) 0.0408 (6)
H21 0.3047 0.5829 −0.2234 0.049*
C22 0.1397 (3) 0.7457 (3) −0.2134 (2) 0.0397 (6)
H22 0.0665 0.7484 −0.2568 0.048*
C23 0.1049 (3) 0.8378 (3) −0.1720 (2) 0.0348 (5)
H23 0.0086 0.9047 −0.1879 0.042*
C24 0.2118 (2) 0.8345 (2) −0.1049 (2) 0.0292 (5)
C25 0.1806 (2) 0.9263 (2) −0.0580 (2) 0.0304 (5)
H25 0.0851 0.9945 −0.0731 0.036*
C26 0.2844 (2) 0.9195 (2) 0.0086 (2) 0.0290 (5)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Sn1 0.01985 (8) 0.01819 (8) 0.03093 (9) −0.00410 (6) 0.00688 (6) −0.00751 (6)
Br1 0.04928 (17) 0.05103 (18) 0.05338 (18) −0.02710 (14) 0.01566 (14) −0.03359 (15)
N1 0.0219 (9) 0.0205 (9) 0.0239 (9) −0.0055 (7) 0.0040 (7) −0.0059 (7)
N2 0.0236 (9) 0.0225 (9) 0.0251 (9) −0.0051 (8) 0.0031 (8) −0.0076 (8)
O1 0.0220 (8) 0.0282 (9) 0.0573 (11) −0.0044 (7) 0.0013 (8) −0.0209 (8)
O2 0.0257 (8) 0.0239 (8) 0.0356 (9) −0.0017 (7) 0.0028 (7) −0.0144 (7)
O3 0.0257 (9) 0.0317 (9) 0.0517 (11) −0.0017 (7) −0.0001 (8) −0.0241 (9)
C1 0.026 (3) 0.035 (3) 0.017 (5) −0.003 (2) 0.003 (2) −0.005 (2)
C2 0.035 (3) 0.042 (3) 0.028 (2) −0.008 (2) 0.009 (2) −0.015 (2)
C3 0.033 (3) 0.034 (3) 0.043 (3) −0.009 (2) 0.007 (2) −0.013 (2)
C4 0.044 (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)
C5 0.0246 (11) 0.0182 (10) 0.0282 (11) −0.0058 (9) 0.0018 (9) −0.0055 (9)
C6 0.0291 (12) 0.0237 (11) 0.0279 (12) −0.0096 (9) 0.0047 (9) −0.0098 (9)
C7 0.0362 (13) 0.0282 (12) 0.0276 (12) −0.0137 (11) 0.0043 (10) −0.0065 (10)
C8 0.0462 (16) 0.0477 (16) 0.0332 (14) −0.0236 (13) 0.0140 (12) −0.0138 (12)
C9 0.0262 (11) 0.0193 (11) 0.0358 (13) −0.0098 (9) 0.0044 (10) −0.0058 (9)
C10 0.0287 (12) 0.0214 (12) 0.0467 (15) −0.0096 (10) −0.0042 (11) −0.0048 (11)
C11 0.0391 (14) 0.0257 (12) 0.0362 (13) −0.0196 (11) −0.0023 (11) −0.0040 (10)
C12 0.0376 (13) 0.0255 (12) 0.0331 (13) −0.0176 (10) 0.0083 (10) −0.0101 (10)
C13 0.0289 (12) 0.0236 (11) 0.0304 (12) −0.0112 (10) 0.0088 (10) −0.0085 (10)
C14 0.0257 (11) 0.0199 (11) 0.0253 (11) −0.0087 (9) 0.0052 (9) −0.0041 (9)
C15 0.0208 (10) 0.0189 (11) 0.0286 (11) −0.0047 (9) 0.0054 (9) −0.0058 (9)
C16 0.0252 (11) 0.0211 (11) 0.0235 (11) −0.0081 (9) 0.0075 (9) −0.0051 (9)
C17 0.0272 (11) 0.0206 (11) 0.0224 (11) −0.0081 (9) 0.0070 (9) −0.0048 (9)
C18 0.0249 (11) 0.0217 (11) 0.0214 (11) −0.0056 (9) 0.0054 (9) −0.0050 (9)
C19 0.0331 (12) 0.0248 (11) 0.0183 (10) −0.0100 (10) 0.0064 (9) −0.0039 (9)
C20 0.0360 (13) 0.0290 (13) 0.0267 (12) −0.0074 (10) 0.0035 (10) −0.0103 (10)
C21 0.0510 (16) 0.0361 (14) 0.0293 (13) −0.0142 (12) 0.0016 (12) −0.0130 (11)
C22 0.0425 (15) 0.0428 (15) 0.0271 (13) −0.0187 (12) 0.0000 (11) −0.0092 (11)
C23 0.0318 (13) 0.0340 (13) 0.0252 (12) −0.0129 (11) 0.0025 (10) −0.0038 (10)
C24 0.0297 (12) 0.0242 (11) 0.0217 (11) −0.0108 (10) 0.0058 (9) −0.0022 (9)
C25 0.0241 (11) 0.0237 (11) 0.0302 (12) −0.0069 (9) 0.0066 (9) −0.0058 (9)
C26 0.0290 (12) 0.0220 (11) 0.0281 (12) −0.0087 (9) 0.0094 (10) −0.0084 (9)
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Geometric parameters (Å, °)

Sn1—O1 2.0857 (17) C5—H5B 0.9900
Sn1—C1 2.089 (15) C6—C7 1.525 (3)
Sn1—C5 2.126 (2) C6—H6A 0.9900
Sn1—O2 2.1531 (16) C6—H6B 0.9900
Sn1—C1' 2.20 (2) C7—C8 1.522 (3)
Sn1—N1 2.1932 (18) C7—H7A 0.9900
Br1—C12 1.895 (2) C7—H7B 0.9900
N1—C15 1.296 (3) C8—H8A 0.9800
N1—N2 1.389 (2) C8—H8B 0.9800
N2—C16 1.316 (3) C8—H8C 0.9800
O1—C9 1.319 (3) C9—C10 1.405 (3)
O2—C16 1.295 (3) C9—C14 1.417 (3)
O3—C26 1.353 (3) C10—C11 1.373 (4)
O3—H3 0.830 (10) C10—H10 0.9500
C1—C2 1.538 (7) C11—C12 1.389 (3)
C1—H1A 0.9900 C11—H11 0.9500
C1—H1B 0.9900 C12—C13 1.369 (3)
C2—C3 1.507 (6) C13—C14 1.415 (3)
C2—H2A 0.9900 C13—H13 0.9500
C2—H2B 0.9900 C14—C15 1.429 (3)
C3—C4 1.566 (7) C15—H15 0.9500
C3—H3A 0.9900 C16—C17 1.474 (3)
C3—H3B 0.9900 C17—C18 1.377 (3)
C4—H4A 0.9800 C17—C26 1.437 (3)
C4—H4B 0.9800 C18—C19 1.408 (3)
C4—H4C 0.9800 C18—H18 0.9500
C1'—C2' 1.538 (9) C19—C20 1.419 (3)
C1'—H1C 0.9900 C19—C24 1.424 (3)
C1'—H1D 0.9900 C20—C21 1.367 (3)
C2'—C3' 1.516 (8) C20—H20 0.9500
C2'—H2C 0.9900 C21—C22 1.414 (4)
C2'—H2D 0.9900 C21—H21 0.9500
C3'—C4' 1.563 (9) C22—C23 1.359 (4)
C3'—H3C 0.9900 C22—H22 0.9500
C3'—H3D 0.9900 C23—C24 1.422 (3)
C4'—H4D 0.9800 C23—H23 0.9500
C4'—H4E 0.9800 C24—C25 1.412 (3)
C4'—H4F 0.9800 C25—C26 1.369 (3)
C5—C6 1.525 (3) C25—H25 0.9500
C5—H5A 0.9900
O1—Sn1—C1 90.6 (3) C7—C6—H6A 109.2
O1—Sn1—C5 97.48 (8) C5—C6—H6A 109.2
C1—Sn1—C5 126.0 (2) C7—C6—H6B 109.2
O1—Sn1—O2 153.97 (6) C5—C6—H6B 109.2
C1—Sn1—O2 98.7 (3) H6A—C6—H6B 107.9
C5—Sn1—O2 96.49 (8) C8—C7—C6 112.7 (2)
O1—Sn1—C1' 98.9 (4) C8—C7—H7A 109.0
C1—Sn1—C1' 9.2 (6) C6—C7—H7A 109.0
C5—Sn1—C1' 128.1 (2) C8—C7—H7B 109.0
O2—Sn1—C1' 89.5 (4) C6—C7—H7B 109.0
O1—Sn1—N1 82.45 (6) H7A—C7—H7B 107.8
C1—Sn1—N1 128.2 (2) C7—C8—H8A 109.5
C5—Sn1—N1 105.82 (7) C7—C8—H8B 109.5
O2—Sn1—N1 72.64 (6) H8A—C8—H8B 109.5
C1'—Sn1—N1 124.9 (2) C7—C8—H8C 109.5
C15—N1—N2 115.59 (18) H8A—C8—H8C 109.5
C15—N1—Sn1 128.43 (15) H8B—C8—H8C 109.5
N2—N1—Sn1 115.90 (13) O1—C9—C10 118.8 (2)
C16—N2—N1 112.44 (17) O1—C9—C14 123.1 (2)
C9—O1—Sn1 133.15 (15) C10—C9—C14 118.1 (2)
C16—O2—Sn1 115.23 (14) C11—C10—C9 121.5 (2)
C26—O3—H3 110 (2) C11—C10—H10 119.3
C2—C1—Sn1 114.9 (8) C9—C10—H10 119.3
C2—C1—H1A 108.5 C10—C11—C12 120.1 (2)
Sn1—C1—H1A 108.5 C10—C11—H11 119.9
C2—C1—H1B 108.5 C12—C11—H11 119.9
Sn1—C1—H1B 108.5 C13—C12—C11 120.5 (2)
H1A—C1—H1B 107.5 C13—C12—Br1 120.52 (18)
C3—C2—C1 113.6 (6) C11—C12—Br1 118.98 (18)
C3—C2—H2A 108.8 C12—C13—C14 120.4 (2)
C1—C2—H2A 108.8 C12—C13—H13 119.8
C3—C2—H2B 108.8 C14—C13—H13 119.8
C1—C2—H2B 108.8 C13—C14—C9 119.4 (2)
H2A—C2—H2B 107.7 C13—C14—C15 116.9 (2)
C2—C3—C4 110.1 (6) C9—C14—C15 123.7 (2)
C2—C3—H3A 109.6 N1—C15—C14 126.7 (2)
C4—C3—H3A 109.6 N1—C15—H15 116.7
C2—C3—H3B 109.6 C14—C15—H15 116.7
C4—C3—H3B 109.6 O2—C16—N2 123.8 (2)
H3A—C3—H3B 108.2 O2—C16—C17 118.5 (2)
C2'—C1'—Sn1 111.5 (10) N2—C16—C17 117.68 (19)
C2'—C1'—H1C 109.3 C18—C17—C26 118.6 (2)
Sn1—C1'—H1C 109.3 C18—C17—C16 118.82 (19)
C2'—C1'—H1D 109.3 C26—C17—C16 122.6 (2)
Sn1—C1'—H1D 109.3 C17—C18—C19 122.5 (2)
H1C—C1'—H1D 108.0 C17—C18—H18 118.7
C3'—C2'—C1' 112.8 (8) C19—C18—H18 118.7
C3'—C2'—H2C 109.0 C18—C19—C20 122.1 (2)
C1'—C2'—H2C 109.0 C18—C19—C24 118.3 (2)
C3'—C2'—H2D 109.0 C20—C19—C24 119.6 (2)
C1'—C2'—H2D 109.0 C21—C20—C19 120.5 (2)
H2C—C2'—H2D 107.8 C21—C20—H20 119.7
C2'—C3'—C4' 109.0 (7) C19—C20—H20 119.7
C2'—C3'—H3C 109.9 C20—C21—C22 119.6 (2)
C4'—C3'—H3C 109.9 C20—C21—H21 120.2
C2'—C3'—H3D 109.9 C22—C21—H21 120.2
C4'—C3'—H3D 109.9 C23—C22—C21 121.5 (2)
H3C—C3'—H3D 108.3 C23—C22—H22 119.3
C3'—C4'—H4D 109.5 C21—C22—H22 119.3
C3'—C4'—H4E 109.5 C22—C23—C24 120.4 (2)
H4D—C4'—H4E 109.5 C22—C23—H23 119.8
C3'—C4'—H4F 109.5 C24—C23—H23 119.8
H4D—C4'—H4F 109.5 C25—C24—C23 122.6 (2)
H4E—C4'—H4F 109.5 C25—C24—C19 119.1 (2)
C6—C5—Sn1 113.65 (14) C23—C24—C19 118.3 (2)
C6—C5—H5A 108.8 C26—C25—C24 121.6 (2)
Sn1—C5—H5A 108.8 C26—C25—H25 119.2
C6—C5—H5B 108.8 C24—C25—H25 119.2
Sn1—C5—H5B 108.8 O3—C26—C25 118.2 (2)
H5A—C5—H5B 107.7 O3—C26—C17 121.9 (2)
C7—C6—C5 112.22 (19) C25—C26—C17 119.9 (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—C13 0.8 (4)
C5—Sn1—N1—C15 85.7 (2) C10—C11—C12—Br1 −178.50 (18)
O2—Sn1—N1—C15 177.7 (2) C11—C12—C13—C14 0.6 (3)
C1'—Sn1—N1—C15 −105.6 (5) Br1—C12—C13—C14 179.89 (16)
O1—Sn1—N1—N2 173.53 (15) C12—C13—C14—C9 −1.4 (3)
C1—Sn1—N1—N2 88.7 (4) C12—C13—C14—C15 179.8 (2)
C5—Sn1—N1—N2 −90.79 (15) O1—C9—C14—C13 −177.6 (2)
O2—Sn1—N1—N2 1.18 (13) C10—C9—C14—C13 0.8 (3)
C1'—Sn1—N1—N2 77.9 (5) O1—C9—C14—C15 1.1 (4)
C15—N1—N2—C16 −178.12 (19) C10—C9—C14—C15 179.5 (2)
Sn1—N1—N2—C16 −1.1 (2) N2—N1—C15—C14 178.17 (19)
C1—Sn1—O1—C9 146.5 (3) Sn1—N1—C15—C14 1.6 (3)
C5—Sn1—O1—C9 −87.0 (2) C13—C14—C15—N1 −175.1 (2)
O2—Sn1—O1—C9 34.9 (3) C9—C14—C15—N1 6.1 (4)
C1'—Sn1—O1—C9 142.4 (3) Sn1—O2—C16—N2 0.9 (3)
N1—Sn1—O1—C9 18.1 (2) Sn1—O2—C16—C17 −178.28 (14)
O1—Sn1—O2—C16 −18.6 (2) N1—N2—C16—O2 0.2 (3)
C1—Sn1—O2—C16 −128.4 (3) N1—N2—C16—C17 179.36 (17)
C5—Sn1—O2—C16 103.52 (16) O2—C16—C17—C18 −0.9 (3)
C1'—Sn1—O2—C16 −128.1 (3) N2—C16—C17—C18 179.84 (19)
N1—Sn1—O2—C16 −1.07 (14) O2—C16—C17—C26 177.4 (2)
O1—Sn1—C1—C2 137.0 (6) N2—C16—C17—C26 −1.8 (3)
C5—Sn1—C1—C2 37.3 (8) C26—C17—C18—C19 −0.9 (3)
O2—Sn1—C1—C2 −67.4 (7) C16—C17—C18—C19 177.48 (19)
C1'—Sn1—C1—C2 −69 (3) C17—C18—C19—C20 −179.3 (2)
N1—Sn1—C1—C2 −142.1 (5) C17—C18—C19—C24 0.1 (3)
Sn1—C1—C2—C3 −59.5 (10) C18—C19—C20—C21 177.6 (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—C22 1.3 (4)
C1—Sn1—C1'—C2' 59 (2) C20—C21—C22—C23 0.2 (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—C19 0.6 (3)
Sn1—C1'—C2'—C3' 67.2 (12) C18—C19—C24—C25 0.9 (3)
C1'—C2'—C3'—C4' −178.6 (11) C20—C19—C24—C25 −179.7 (2)
O1—Sn1—C5—C6 68.73 (16) C18—C19—C24—C23 −178.6 (2)
C1—Sn1—C5—C6 165.0 (4) C20—C19—C24—C23 0.8 (3)
O2—Sn1—C5—C6 −89.24 (16) C23—C24—C25—C26 178.5 (2)
C1'—Sn1—C5—C6 176.3 (5) C19—C24—C25—C26 −1.0 (3)
N1—Sn1—C5—C6 −15.50 (18) C24—C25—C26—O3 179.3 (2)
Sn1—C5—C6—C7 −179.63 (15) C24—C25—C26—C17 0.1 (3)
C5—C6—C7—C8 −179.5 (2) C18—C17—C26—O3 −178.3 (2)
Sn1—O1—C9—C10 164.47 (17) C16—C17—C26—O3 3.3 (3)
Sn1—O1—C9—C14 −17.1 (3) C18—C17—C26—C25 0.8 (3)
O1—C9—C10—C11 179.1 (2) C16—C17—C26—C25 −177.5 (2)
C14—C9—C10—C11 0.6 (4)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O3—H3···N2 0.83 (1) 1.88 (2) 2.606 (2) 146 (3)
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Footnotes

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

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. Labib, L., Khalil, T. E., Iskander, M. F. & Refaat, L. S. (1996). Polyhedron, 21, 3697–3707.
  4. Samanta, B., Chakraborty, J., Dey, D. K. & Mitra, S. (2007). Struct. Chem.18, 287–297.
  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. (2009). publCIF In preparation.

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/S1600536809024477/xu2544sup1.cif

e-65-0m862-sup1.cif (26.2KB, cif)

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

e-65-0m862-Isup2.hkl (281KB, 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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