Literature DB >> 21836941

{4-Hy-droxy-N'-[(2E,3Z)-4-oxido-4-phenyl-but-3-en-2-yl-idene]benzo-hydra-zidato}diphenyl-tin(IV) methanol monosolvate.

Md Abu Affan, Norrihan B Sam, Fasihuddin B Ahmad, Fraser White, Edward R T Tiekink.   

Abstract

Two independent diphenyl-tin mol-ecules and two independent methanol mol-ecules comprise the asymmetric unit of the title compound, [Sn(C(6)H(5))(2)(C(17)H(14)N(2)O(3))]·CH(3)OH. The Sn atom in each is five-coordinated by a tridentate ligand and the ipso-C atoms of the Sn-bound benzene substituents. The resulting C(2)N(2)O donor set defines a coordination geometry that is inter-mediate between trigonal-bipyramidal (TP) and square-pyramidal (SP), with one mol-ecule slightly tending towards TP and the other slightly towards SP. The mol-ecules differ in terms of the relative orientations of the terminal benzene rings [dihedral angles = 45.71 (18) and 53.98 (17)°] and of the Sn-bound benzene substituents [dihedral angles = 59.5 (2) and 45.77 (18)°, respectively]. The most prominent feature of the crystal packing is the formation of four-mol-ecule aggregates via O-H⋯O and O-H⋯N hydrogen bonds, in which the hy-droxy group is connected to a methanol mol-ecule which, in turn, is linked to a non-coordinating N atom. Weak C-H⋯π inter-actions also occur.

Entities:  

Year:  2011        PMID: 21836941      PMCID: PMC3151954          DOI: 10.1107/S1600536811023415

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For background to the biological inter­est in related compounds, see: Affan et al. (2010 ▶). For related structures, see: Affan et al. (2009 ▶, 2011 ▶). For additional structural analysis, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Sn(C6H5)2(<span class="Gene">C17<span class="Species">H14N2O3)]·CH4O M = 599.23 Monoclinic, a = 18.6824 (2) Å b = 28.7280 (4) Å c = 10.3369 (1) Å β = 99.856 (1)° V = 5466.02 (11) Å3 Z = 8 Cu Kα radiation μ = 7.74 mm−1 T = 150 K 0.37 × 0.29 × 0.17 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.231, T max = 0.611 17500 measured reflections 9175 independent reflections 8138 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.079 S = 1.00 9175 reflections 675 parameters H-atom parameters constrained Δρmax = 0.46 e Å−3 Δρmin = −0.58 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), <span class="Disease">DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: PLATON (<span class="Chemical">Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023415/hb5914sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023415/hb5914Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Sn(C6H5)2(C17H14N2O3)]·CH4OF(000) = 2432
Mr = 599.23Dx = 1.456 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 10187 reflections
a = 18.6824 (2) Åθ = 3.1–74.5°
b = 28.7280 (4) ŵ = 7.74 mm1
c = 10.3369 (1) ÅT = 150 K
β = 99.856 (1)°Block, yellow
V = 5466.02 (11) Å30.37 × 0.29 × 0.17 mm
Z = 8
Agilent SuperNova Dual Cu at zero Atlas diffractometer9175 independent reflections
Radiation source: SuperNova (Cu) X-ray Source8138 reflections with I > 2σ(I)
mirrorRint = 0.036
ω scansθmax = 65.0°, θmin = 3.1°
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)h = −21→21
Tmin = 0.231, Tmax = 0.611k = −27→33
17500 measured reflectionsl = −12→11
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0362P)2] where P = (Fo2 + 2Fc2)/3
9175 reflections(Δ/σ)max = 0.002
675 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.58 e Å3
Experimental. Agilent Technologies (2011) CrysAlis PRO Software system, version 1.171.34.49, Agilent Technologies UK Ltd, Oxford, UK
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
Sn10.913726 (11)0.613291 (8)0.89734 (2)0.02462 (7)
O10.88488 (11)0.55161 (8)0.9894 (2)0.0312 (5)
O20.84683 (13)0.42008 (9)1.4635 (2)0.0372 (6)
H2O0.88170.41371.52360.056*
O30.98171 (11)0.66440 (8)0.8377 (2)0.0296 (5)
N11.00051 (14)0.55638 (10)1.1106 (2)0.0267 (6)
N21.01155 (13)0.58776 (10)1.0125 (2)0.0250 (6)
C10.93374 (17)0.53974 (12)1.0898 (3)0.0265 (7)
C20.91311 (16)0.50704 (11)1.1859 (3)0.0245 (7)
C30.84140 (17)0.49194 (12)1.1748 (3)0.0285 (7)
H30.80640.50211.10260.034*
C40.82033 (18)0.46251 (13)1.2667 (3)0.0307 (8)
H40.77110.45281.25770.037*
C50.87068 (17)0.44702 (12)1.3725 (3)0.0290 (7)
C60.94380 (18)0.46045 (12)1.3823 (3)0.0309 (8)
H60.97910.44941.45280.037*
C70.96428 (17)0.48969 (12)1.2893 (3)0.0300 (8)
H71.01390.49821.29560.036*
C81.07935 (16)0.59773 (12)1.0015 (3)0.0256 (7)
C91.14014 (17)0.57482 (13)1.0926 (3)0.0317 (8)
H9A1.14150.58671.18190.048*
H9B1.18640.58171.06390.048*
H9C1.13230.54111.09180.048*
C101.09663 (17)0.62921 (12)0.9064 (3)0.0273 (7)
H101.14600.62970.89460.033*
C111.05056 (17)0.65907 (12)0.8290 (3)0.0265 (7)
C121.07698 (17)0.68986 (13)0.7317 (3)0.0303 (8)
C131.13904 (19)0.67964 (14)0.6808 (3)0.0374 (9)
H131.16530.65190.70730.045*
C141.1632 (2)0.70882 (16)0.5929 (4)0.0492 (11)
H141.20620.70130.55990.059*
C151.1258 (2)0.74874 (18)0.5519 (5)0.0609 (14)
H151.14320.76920.49210.073*
C161.0627 (2)0.75882 (17)0.5988 (5)0.0606 (13)
H161.03590.78610.56970.073*
C171.0382 (2)0.72947 (15)0.6878 (4)0.0456 (10)
H170.99450.73650.71890.055*
C180.85967 (17)0.66046 (13)1.0053 (3)0.0309 (8)
C190.8137 (2)0.64476 (16)1.0884 (4)0.0427 (9)
H190.80830.61221.10000.051*
C200.7761 (2)0.67520 (19)1.1540 (4)0.0555 (12)
H200.74450.66391.20970.067*
C210.7849 (2)0.7226 (2)1.1382 (5)0.0691 (16)
H210.76010.74391.18510.083*
C220.8298 (2)0.73929 (17)1.0541 (6)0.0684 (15)
H220.83480.77181.04210.082*
C230.8670 (2)0.70802 (15)0.9878 (5)0.0494 (11)
H230.89770.71920.93020.059*
C240.87277 (17)0.59245 (12)0.7023 (3)0.0290 (7)
C250.8810 (3)0.62217 (15)0.6003 (4)0.0578 (13)
H250.90560.65100.61850.069*
C260.8534 (3)0.60990 (18)0.4715 (4)0.0714 (16)
H260.85980.63000.40140.086*
C270.8168 (2)0.56845 (16)0.4456 (4)0.0517 (11)
H270.79650.56060.35760.062*
C280.8093 (2)0.53846 (16)0.5448 (4)0.0470 (10)
H280.78530.50950.52570.056*
C290.83686 (18)0.55053 (14)0.6737 (4)0.0368 (8)
H290.83110.52990.74300.044*
Sn20.544563 (10)0.625910 (7)0.42618 (2)0.02395 (7)
O40.58497 (11)0.56399 (8)0.5247 (2)0.0294 (5)
O50.67111 (12)0.44090 (9)1.0327 (2)0.0362 (6)
H5O0.64010.42911.07300.054*
O60.46618 (11)0.67353 (8)0.3385 (2)0.0275 (5)
N30.47311 (14)0.56128 (10)0.5916 (3)0.0266 (6)
N40.45350 (13)0.59189 (10)0.4855 (3)0.0263 (6)
C300.54222 (17)0.54933 (12)0.6031 (3)0.0265 (7)
C310.57345 (17)0.51907 (11)0.7128 (3)0.0263 (7)
C320.53045 (17)0.49582 (12)0.7912 (3)0.0296 (7)
H320.47910.49830.77060.035*
C330.56147 (17)0.46943 (12)0.8975 (3)0.0302 (7)
H330.53160.45410.94990.036*
C340.63680 (18)0.46532 (12)0.9277 (3)0.0289 (7)
C350.67993 (18)0.48745 (12)0.8492 (3)0.0315 (8)
H350.73130.48450.86900.038*
C360.64864 (17)0.51351 (12)0.7431 (3)0.0293 (7)
H360.67870.52800.68950.035*
C370.38430 (16)0.59648 (12)0.4367 (3)0.0254 (7)
C380.32879 (17)0.56738 (13)0.4907 (3)0.0344 (8)
H38A0.34670.53540.50440.052*
H38B0.28300.56740.42810.052*
H38C0.32070.58050.57450.052*
C390.36003 (17)0.62742 (12)0.3309 (3)0.0287 (7)
H390.31130.62360.28730.034*
C400.39911 (16)0.66212 (12)0.2850 (3)0.0256 (7)
C410.36756 (16)0.69069 (12)0.1693 (3)0.0265 (7)
C420.31586 (18)0.67235 (14)0.0691 (3)0.0364 (8)
H420.29910.64130.07520.044*
C430.2888 (2)0.69927 (16)−0.0395 (4)0.0457 (10)
H430.25340.6865−0.10720.055*
C440.31245 (19)0.74418 (15)−0.0508 (4)0.0403 (9)
H440.29370.7624−0.12560.048*
C450.3634 (2)0.76235 (15)0.0472 (4)0.0416 (9)
H450.38010.79340.04020.050*
C460.39095 (19)0.73594 (13)0.1562 (3)0.0345 (8)
H460.42640.74900.22320.041*
C470.58271 (17)0.60961 (12)0.2503 (3)0.0278 (7)
C480.55966 (19)0.63494 (14)0.1365 (3)0.0363 (8)
H480.52590.65970.13680.044*
C490.5859 (2)0.62421 (15)0.0219 (4)0.0431 (10)
H490.57070.6419−0.05560.052*
C500.6342 (2)0.58782 (16)0.0211 (4)0.0460 (10)
H500.65190.5804−0.05730.055*
C510.6567 (2)0.56233 (15)0.1331 (4)0.0451 (10)
H510.68970.53730.13170.054*
C520.63146 (19)0.57301 (13)0.2479 (4)0.0356 (8)
H520.64740.55540.32520.043*
C530.59273 (16)0.66994 (12)0.5821 (3)0.0271 (7)
C540.5622 (2)0.71212 (14)0.6050 (4)0.0415 (9)
H540.52270.72390.54350.050*
C550.5886 (2)0.73760 (16)0.7175 (4)0.0529 (11)
H550.56630.76630.73320.064*
C560.6464 (2)0.72180 (15)0.8055 (4)0.0456 (10)
H560.66420.73940.88210.055*
C570.6786 (2)0.68048 (15)0.7829 (4)0.0443 (10)
H570.71920.66970.84350.053*
C580.65233 (19)0.65424 (14)0.6718 (4)0.0394 (9)
H580.67500.62560.65690.047*
O70.58272 (16)0.40602 (10)0.1873 (3)0.0475 (7)
H7O0.57260.42030.25280.071*
C590.5821 (3)0.3582 (2)0.2101 (6)0.0833 (17)
H59A0.62860.34880.26280.125*
H59B0.57490.34160.12610.125*
H59C0.54250.35060.25760.125*
O80.04591 (17)0.60516 (10)0.3473 (3)0.0524 (8)
H8O0.03520.59010.27700.079*
C600.0200 (4)0.6484 (2)0.3296 (6)0.107 (2)
H60A0.02450.66410.41470.160*
H60B−0.03130.64730.28840.160*
H60C0.04770.66550.27270.160*
U11U22U33U12U13U23
Sn10.02344 (11)0.02432 (12)0.02486 (11)0.00139 (8)0.00064 (8)0.00269 (8)
O10.0285 (11)0.0309 (13)0.0315 (12)−0.0008 (10)−0.0028 (10)0.0085 (11)
O20.0355 (13)0.0391 (15)0.0374 (13)−0.0022 (11)0.0074 (11)0.0120 (12)
O30.0251 (11)0.0279 (13)0.0358 (12)0.0005 (9)0.0052 (10)0.0062 (10)
N10.0267 (13)0.0278 (15)0.0257 (13)0.0004 (12)0.0043 (11)0.0065 (12)
N20.0243 (13)0.0241 (15)0.0260 (13)0.0031 (11)0.0027 (11)0.0045 (11)
C10.0268 (16)0.0241 (17)0.0284 (16)0.0031 (13)0.0045 (14)−0.0011 (14)
C20.0261 (16)0.0223 (17)0.0248 (16)0.0013 (13)0.0033 (13)−0.0003 (13)
C30.0253 (16)0.0310 (19)0.0282 (16)0.0019 (14)0.0014 (13)0.0009 (15)
C40.0271 (16)0.035 (2)0.0303 (17)−0.0036 (14)0.0058 (14)0.0004 (15)
C50.0318 (17)0.0277 (18)0.0284 (17)−0.0012 (14)0.0080 (14)0.0021 (15)
C60.0299 (17)0.0313 (19)0.0301 (17)−0.0007 (14)0.0014 (14)0.0045 (15)
C70.0233 (16)0.032 (2)0.0326 (17)−0.0033 (14)−0.0004 (14)0.0047 (15)
C80.0254 (16)0.0274 (18)0.0238 (15)0.0025 (13)0.0033 (13)−0.0022 (14)
C90.0267 (16)0.034 (2)0.0345 (18)0.0035 (14)0.0048 (14)0.0078 (16)
C100.0254 (16)0.0298 (19)0.0270 (16)0.0001 (13)0.0055 (13)0.0021 (14)
C110.0305 (17)0.0251 (18)0.0236 (16)−0.0024 (14)0.0037 (13)−0.0037 (14)
C120.0305 (17)0.0316 (19)0.0273 (16)−0.0035 (14)0.0007 (14)0.0065 (15)
C130.0359 (19)0.042 (2)0.0328 (18)−0.0054 (17)0.0022 (16)0.0101 (17)
C140.039 (2)0.066 (3)0.043 (2)−0.002 (2)0.0076 (18)0.018 (2)
C150.047 (2)0.070 (3)0.065 (3)−0.006 (2)0.010 (2)0.038 (3)
C160.054 (3)0.053 (3)0.074 (3)0.007 (2)0.010 (2)0.035 (3)
C170.041 (2)0.044 (2)0.052 (2)0.0016 (18)0.0099 (18)0.017 (2)
C180.0238 (15)0.037 (2)0.0308 (17)0.0026 (14)0.0015 (14)−0.0012 (15)
C190.039 (2)0.053 (3)0.035 (2)0.0079 (18)0.0040 (17)0.0037 (19)
C200.048 (2)0.080 (4)0.044 (2)0.010 (2)0.0208 (19)−0.008 (2)
C210.050 (3)0.085 (4)0.075 (3)0.013 (3)0.015 (2)−0.044 (3)
C220.050 (3)0.042 (3)0.114 (4)0.005 (2)0.016 (3)−0.029 (3)
C230.038 (2)0.039 (2)0.074 (3)−0.0014 (17)0.018 (2)−0.011 (2)
C240.0308 (16)0.0282 (18)0.0266 (16)0.0033 (14)0.0012 (14)−0.0028 (14)
C250.092 (3)0.038 (2)0.036 (2)−0.018 (2)−0.010 (2)0.0094 (19)
C260.111 (4)0.061 (3)0.035 (2)−0.020 (3)−0.011 (3)0.010 (2)
C270.058 (3)0.060 (3)0.033 (2)−0.006 (2)−0.0027 (19)−0.013 (2)
C280.048 (2)0.050 (3)0.043 (2)−0.016 (2)0.0094 (19)−0.015 (2)
C290.0353 (19)0.038 (2)0.0384 (19)−0.0087 (16)0.0110 (16)0.0006 (17)
Sn20.02155 (11)0.02523 (12)0.02636 (11)0.00062 (8)0.00779 (8)0.00407 (9)
O40.0268 (11)0.0286 (13)0.0354 (12)0.0052 (10)0.0127 (10)0.0096 (10)
O50.0348 (12)0.0356 (15)0.0378 (14)0.0066 (11)0.0049 (11)0.0128 (11)
O60.0223 (10)0.0278 (13)0.0315 (12)−0.0006 (9)0.0024 (9)0.0048 (10)
N30.0253 (13)0.0280 (16)0.0275 (14)0.0017 (11)0.0073 (11)0.0074 (12)
N40.0254 (13)0.0249 (15)0.0289 (14)−0.0005 (11)0.0059 (11)0.0034 (12)
C300.0280 (16)0.0235 (17)0.0292 (16)−0.0001 (13)0.0083 (14)−0.0004 (14)
C310.0293 (16)0.0219 (17)0.0280 (16)0.0015 (13)0.0058 (14)0.0008 (14)
C320.0247 (16)0.0287 (19)0.0355 (18)−0.0004 (14)0.0057 (14)0.0052 (15)
C330.0302 (17)0.0280 (19)0.0329 (17)−0.0021 (14)0.0072 (14)0.0068 (15)
C340.0349 (18)0.0228 (17)0.0292 (17)0.0033 (14)0.0061 (14)−0.0008 (14)
C350.0265 (16)0.033 (2)0.0362 (18)0.0057 (14)0.0079 (14)0.0016 (16)
C360.0291 (17)0.0262 (18)0.0352 (18)0.0031 (14)0.0124 (14)0.0020 (15)
C370.0219 (15)0.0260 (18)0.0298 (16)−0.0012 (13)0.0087 (13)−0.0013 (14)
C380.0264 (17)0.040 (2)0.0382 (19)−0.0060 (15)0.0086 (15)0.0058 (17)
C390.0239 (16)0.0326 (19)0.0296 (17)−0.0001 (14)0.0047 (14)0.0011 (15)
C400.0273 (16)0.0261 (17)0.0243 (15)0.0048 (13)0.0071 (13)−0.0026 (14)
C410.0219 (15)0.0322 (19)0.0269 (16)0.0030 (13)0.0090 (13)0.0000 (14)
C420.0364 (18)0.034 (2)0.0373 (19)−0.0017 (16)0.0013 (16)0.0018 (16)
C430.041 (2)0.060 (3)0.0327 (19)−0.0002 (19)−0.0038 (17)0.0026 (19)
C440.0338 (19)0.056 (3)0.0326 (19)0.0110 (18)0.0101 (16)0.0173 (18)
C450.042 (2)0.041 (2)0.043 (2)−0.0024 (17)0.0100 (18)0.0155 (18)
C460.0343 (18)0.035 (2)0.0330 (18)−0.0053 (15)0.0025 (15)0.0073 (16)
C470.0269 (16)0.0313 (19)0.0270 (16)−0.0050 (14)0.0096 (14)−0.0030 (14)
C480.0356 (19)0.040 (2)0.0351 (19)−0.0049 (16)0.0098 (16)0.0001 (17)
C490.049 (2)0.051 (3)0.0305 (19)−0.0133 (19)0.0100 (17)−0.0024 (18)
C500.052 (2)0.054 (3)0.037 (2)−0.011 (2)0.0229 (18)−0.017 (2)
C510.044 (2)0.042 (2)0.054 (2)0.0010 (18)0.0232 (19)−0.012 (2)
C520.0373 (19)0.032 (2)0.0389 (19)−0.0010 (16)0.0121 (16)−0.0008 (16)
C530.0223 (15)0.0326 (19)0.0266 (16)−0.0048 (13)0.0055 (13)0.0018 (14)
C540.0348 (19)0.038 (2)0.047 (2)0.0061 (17)−0.0053 (17)−0.0040 (18)
C550.048 (2)0.044 (3)0.063 (3)0.001 (2)0.000 (2)−0.019 (2)
C560.046 (2)0.047 (3)0.043 (2)−0.0163 (19)0.0046 (18)−0.0058 (19)
C570.038 (2)0.050 (3)0.039 (2)−0.0063 (18)−0.0080 (17)0.0108 (19)
C580.0358 (19)0.037 (2)0.043 (2)0.0045 (16)−0.0006 (17)0.0052 (17)
O70.0659 (18)0.0409 (16)0.0417 (15)0.0091 (14)0.0260 (14)0.0102 (13)
C590.096 (4)0.078 (4)0.082 (4)0.019 (3)0.033 (3)0.006 (3)
O80.0736 (19)0.0423 (17)0.0349 (14)0.0028 (15)−0.0089 (14)0.0018 (13)
C600.123 (5)0.087 (5)0.089 (4)0.028 (4)−0.040 (4)−0.027 (4)
Sn1—O12.124 (2)O4—C301.302 (4)
Sn1—O32.102 (2)O5—C341.357 (4)
Sn1—N22.133 (2)O5—H5O0.8400
Sn1—C182.118 (4)O6—C401.322 (4)
Sn1—C242.117 (3)N3—C301.322 (4)
O1—C11.305 (4)N3—N41.404 (4)
O2—C51.350 (4)N4—C371.312 (4)
O2—H2O0.8400C30—C311.468 (4)
O3—C111.314 (4)C31—C361.395 (4)
N1—C11.319 (4)C31—C321.404 (5)
N1—N21.399 (4)C32—C331.378 (4)
N2—C81.322 (4)C32—H320.9500
C1—C21.466 (5)C33—C341.393 (5)
C2—C31.394 (4)C33—H330.9500
C2—C71.398 (4)C34—C351.392 (5)
C3—C41.379 (5)C35—C361.372 (5)
C3—H30.9500C35—H350.9500
C4—C51.388 (5)C36—H360.9500
C4—H40.9500C37—C391.422 (5)
C5—C61.407 (5)C37—C381.511 (4)
C6—C71.379 (5)C38—H38A0.9800
C6—H60.9500C38—H38B0.9800
C7—H70.9500C38—H38C0.9800
C8—C101.413 (5)C39—C401.368 (5)
C8—C91.498 (4)C39—H390.9500
C9—H9A0.9800C40—C411.486 (4)
C9—H9B0.9800C41—C461.385 (5)
C9—H9C0.9800C41—C421.394 (5)
C10—C111.371 (5)C42—C431.385 (5)
C10—H100.9500C42—H420.9500
C11—C121.486 (5)C43—C441.375 (6)
C12—C171.383 (5)C43—H430.9500
C12—C131.384 (5)C44—C451.370 (5)
C13—C141.368 (5)C44—H440.9500
C13—H130.9500C45—C461.382 (5)
C14—C151.371 (6)C45—H450.9500
C14—H140.9500C46—H460.9500
C15—C161.380 (6)C47—C481.388 (5)
C15—H150.9500C47—C521.394 (5)
C16—C171.382 (6)C48—C491.392 (5)
C16—H160.9500C48—H480.9500
C17—H170.9500C49—C501.381 (6)
C18—C231.388 (5)C49—H490.9500
C18—C191.389 (5)C50—C511.374 (6)
C19—C201.372 (6)C50—H500.9500
C19—H190.9500C51—C521.384 (5)
C20—C211.385 (7)C51—H510.9500
C20—H200.9500C52—H520.9500
C21—C221.392 (7)C53—C541.377 (5)
C21—H210.9500C53—C581.396 (5)
C22—C231.387 (6)C54—C551.391 (5)
C22—H220.9500C54—H540.9500
C23—H230.9500C55—C561.365 (6)
C24—C251.385 (5)C55—H550.9500
C24—C291.385 (5)C56—C571.369 (6)
C25—C261.389 (6)C56—H560.9500
C25—H250.9500C57—C581.391 (5)
C26—C271.377 (6)C57—H570.9500
C26—H260.9500C58—H580.9500
C27—C281.365 (6)O7—C591.394 (6)
C27—H270.9500O7—H7O0.8400
C28—C291.389 (5)C59—H59A0.9800
C28—H280.9500C59—H59B0.9800
C29—H290.9500C59—H59C0.9800
Sn2—O42.123 (2)O8—C601.334 (6)
Sn2—O62.094 (2)O8—H8O0.8400
Sn2—N42.141 (3)C60—H60A0.9800
Sn2—C472.116 (3)C60—H60B0.9800
Sn2—C532.124 (3)C60—H60C0.9800
O3—Sn1—C2493.22 (11)C47—Sn2—N4123.12 (11)
O3—Sn1—C1894.26 (12)C53—Sn2—N4107.98 (11)
C24—Sn1—C18123.74 (12)O4—Sn2—N473.44 (9)
O3—Sn1—O1157.92 (8)C30—O4—Sn2111.35 (19)
C24—Sn1—O196.48 (11)C34—O5—H5O109.5
C18—Sn1—O196.73 (12)C40—O6—Sn2124.2 (2)
O3—Sn1—N284.31 (9)C30—N3—N4110.7 (3)
C24—Sn1—N2124.73 (11)C37—N4—N3118.1 (3)
C18—Sn1—N2111.49 (11)C37—N4—Sn2128.5 (2)
O1—Sn1—N273.86 (9)N3—N4—Sn2113.31 (18)
C1—O1—Sn1112.2 (2)O4—C30—N3123.6 (3)
C5—O2—H2O109.5O4—C30—C31117.9 (3)
C11—O3—Sn1125.9 (2)N3—C30—C31118.5 (3)
C1—N1—N2111.6 (2)C36—C31—C32118.0 (3)
C8—N2—N1117.7 (2)C36—C31—C30119.6 (3)
C8—N2—Sn1128.3 (2)C32—C31—C30122.4 (3)
N1—N2—Sn1114.07 (18)C33—C32—C31121.2 (3)
O1—C1—N1123.3 (3)C33—C32—H32119.4
O1—C1—C2118.5 (3)C31—C32—H32119.4
N1—C1—C2118.2 (3)C32—C33—C34119.7 (3)
C3—C2—C7118.3 (3)C32—C33—H33120.1
C3—C2—C1120.3 (3)C34—C33—H33120.1
C7—C2—C1121.5 (3)O5—C34—C35117.5 (3)
C4—C3—C2121.2 (3)O5—C34—C33122.9 (3)
C4—C3—H3119.4C35—C34—C33119.6 (3)
C2—C3—H3119.4C36—C35—C34120.3 (3)
C3—C4—C5120.3 (3)C36—C35—H35119.8
C3—C4—H4119.8C34—C35—H35119.8
C5—C4—H4119.8C35—C36—C31121.1 (3)
O2—C5—C4118.2 (3)C35—C36—H36119.4
O2—C5—C6122.7 (3)C31—C36—H36119.4
C4—C5—C6119.2 (3)N4—C37—C39121.5 (3)
C7—C6—C5120.0 (3)N4—C37—C38119.7 (3)
C7—C6—H6120.0C39—C37—C38118.8 (3)
C5—C6—H6120.0C37—C38—H38A109.5
C6—C7—C2121.0 (3)C37—C38—H38B109.5
C6—C7—H7119.5H38A—C38—H38B109.5
C2—C7—H7119.5C37—C38—H38C109.5
N2—C8—C10122.3 (3)H38A—C38—H38C109.5
N2—C8—C9119.0 (3)H38B—C38—H38C109.5
C10—C8—C9118.7 (3)C40—C39—C37127.1 (3)
C8—C9—H9A109.5C40—C39—H39116.4
C8—C9—H9B109.5C37—C39—H39116.4
H9A—C9—H9B109.5O6—C40—C39124.0 (3)
C8—C9—H9C109.5O6—C40—C41114.6 (3)
H9A—C9—H9C109.5C39—C40—C41121.3 (3)
H9B—C9—H9C109.5C46—C41—C42118.2 (3)
C11—C10—C8127.6 (3)C46—C41—C40120.6 (3)
C11—C10—H10116.2C42—C41—C40121.2 (3)
C8—C10—H10116.2C43—C42—C41120.1 (4)
O3—C11—C10123.9 (3)C43—C42—H42119.9
O3—C11—C12114.8 (3)C41—C42—H42119.9
C10—C11—C12121.3 (3)C44—C43—C42121.0 (4)
C17—C12—C13118.4 (3)C44—C43—H43119.5
C17—C12—C11119.8 (3)C42—C43—H43119.5
C13—C12—C11121.9 (3)C45—C44—C43119.2 (3)
C14—C13—C12121.0 (4)C45—C44—H44120.4
C14—C13—H13119.5C43—C44—H44120.4
C12—C13—H13119.5C44—C45—C46120.5 (4)
C15—C14—C13120.6 (4)C44—C45—H45119.7
C15—C14—H14119.7C46—C45—H45119.7
C13—C14—H14119.7C41—C46—C45121.0 (3)
C14—C15—C16119.2 (4)C41—C46—H46119.5
C14—C15—H15120.4C45—C46—H46119.5
C16—C15—H15120.4C48—C47—C52119.3 (3)
C15—C16—C17120.3 (4)C48—C47—Sn2120.7 (3)
C15—C16—H16119.8C52—C47—Sn2120.0 (3)
C17—C16—H16119.8C47—C48—C49120.1 (4)
C16—C17—C12120.4 (4)C47—C48—H48119.9
C16—C17—H17119.8C49—C48—H48119.9
C12—C17—H17119.8C50—C49—C48119.9 (4)
C23—C18—C19119.0 (4)C50—C49—H49120.1
C23—C18—Sn1119.6 (3)C48—C49—H49120.1
C19—C18—Sn1121.3 (3)C51—C50—C49120.3 (4)
C20—C19—C18121.5 (4)C51—C50—H50119.8
C20—C19—H19119.3C49—C50—H50119.8
C18—C19—H19119.3C50—C51—C52120.3 (4)
C19—C20—C21119.2 (4)C50—C51—H51119.9
C19—C20—H20120.4C52—C51—H51119.9
C21—C20—H20120.4C51—C52—C47120.1 (4)
C20—C21—C22120.6 (4)C51—C52—H52119.9
C20—C21—H21119.7C47—C52—H52119.9
C22—C21—H21119.7C54—C53—C58118.5 (3)
C23—C22—C21119.5 (5)C54—C53—Sn2121.4 (2)
C23—C22—H22120.3C58—C53—Sn2119.8 (3)
C21—C22—H22120.3C53—C54—C55120.5 (3)
C22—C23—C18120.3 (4)C53—C54—H54119.7
C22—C23—H23119.9C55—C54—H54119.7
C18—C23—H23119.9C56—C55—C54120.6 (4)
C25—C24—C29119.1 (3)C56—C55—H55119.7
C25—C24—Sn1118.8 (3)C54—C55—H55119.7
C29—C24—Sn1122.1 (3)C55—C56—C57119.7 (4)
C24—C25—C26120.1 (4)C55—C56—H56120.2
C24—C25—H25119.9C57—C56—H56120.2
C26—C25—H25119.9C56—C57—C58120.5 (3)
C27—C26—C25119.8 (4)C56—C57—H57119.7
C27—C26—H26120.1C58—C57—H57119.7
C25—C26—H26120.1C57—C58—C53120.1 (4)
C28—C27—C26120.8 (4)C57—C58—H58119.9
C28—C27—H27119.6C53—C58—H58119.9
C26—C27—H27119.6C59—O7—H7O109.5
C27—C28—C29119.7 (4)O7—C59—H59A109.5
C27—C28—H28120.2O7—C59—H59B109.5
C29—C28—H28120.2H59A—C59—H59B109.5
C24—C29—C28120.5 (4)O7—C59—H59C109.5
C24—C29—H29119.7H59A—C59—H59C109.5
C28—C29—H29119.7H59B—C59—H59C109.5
O6—Sn2—C4794.94 (11)C60—O8—H8O109.5
O6—Sn2—C5396.51 (11)O8—C60—H60A109.5
C47—Sn2—C53128.51 (12)O8—C60—H60B109.5
O6—Sn2—O4156.93 (8)H60A—C60—H60B109.5
C47—Sn2—O494.72 (11)O8—C60—H60C109.5
C53—Sn2—O493.76 (11)H60A—C60—H60C109.5
O6—Sn2—N483.75 (9)H60B—C60—H60C109.5
O3—Sn1—O1—C127.1 (4)O6—Sn2—O4—C30−31.2 (4)
C24—Sn1—O1—C1142.6 (2)C47—Sn2—O4—C30−145.7 (2)
C18—Sn1—O1—C1−92.2 (2)C53—Sn2—O4—C3085.2 (2)
N2—Sn1—O1—C118.2 (2)N4—Sn2—O4—C30−22.5 (2)
C24—Sn1—O3—C11−94.8 (3)C47—Sn2—O6—C4088.0 (2)
C18—Sn1—O3—C11141.0 (2)C53—Sn2—O6—C40−142.3 (2)
O1—Sn1—O3—C1121.3 (4)O4—Sn2—O6—C40−26.4 (4)
N2—Sn1—O3—C1129.8 (2)N4—Sn2—O6—C40−34.8 (2)
C1—N1—N2—C8−162.8 (3)C30—N3—N4—C37160.5 (3)
C1—N1—N2—Sn116.8 (3)C30—N3—N4—Sn2−20.0 (3)
O3—Sn1—N2—C8−16.0 (3)O6—Sn2—N4—C3719.1 (3)
C24—Sn1—N2—C874.0 (3)C47—Sn2—N4—C37−72.7 (3)
C18—Sn1—N2—C8−108.3 (3)C53—Sn2—N4—C37113.9 (3)
O1—Sn1—N2—C8160.7 (3)O4—Sn2—N4—C37−157.5 (3)
O3—Sn1—N2—N1164.4 (2)O6—Sn2—N4—N3−160.4 (2)
C24—Sn1—N2—N1−105.6 (2)C47—Sn2—N4—N3107.8 (2)
C18—Sn1—N2—N172.0 (2)C53—Sn2—N4—N3−65.5 (2)
O1—Sn1—N2—N1−18.9 (2)O4—Sn2—N4—N323.0 (2)
Sn1—O1—C1—N1−16.5 (4)Sn2—O4—C30—N320.9 (4)
Sn1—O1—C1—C2162.1 (2)Sn2—O4—C30—C31−157.0 (2)
N2—N1—C1—O1−0.1 (5)N4—N3—C30—O4−0.7 (5)
N2—N1—C1—C2−178.7 (3)N4—N3—C30—C31177.2 (3)
O1—C1—C2—C3−4.8 (5)O4—C30—C31—C3610.9 (5)
N1—C1—C2—C3173.9 (3)N3—C30—C31—C36−167.1 (3)
O1—C1—C2—C7174.3 (3)O4—C30—C31—C32−170.3 (3)
N1—C1—C2—C7−7.0 (5)N3—C30—C31—C3211.6 (5)
C7—C2—C3—C43.3 (5)C36—C31—C32—C332.0 (5)
C1—C2—C3—C4−177.7 (3)C30—C31—C32—C33−176.8 (3)
C2—C3—C4—C5−0.4 (5)C31—C32—C33—C34−0.5 (5)
C3—C4—C5—O2176.8 (3)C32—C33—C34—O5178.3 (3)
C3—C4—C5—C6−2.1 (5)C32—C33—C34—C35−0.8 (5)
O2—C5—C6—C7−177.1 (3)O5—C34—C35—C36−178.6 (3)
C4—C5—C6—C71.8 (5)C33—C34—C35—C360.5 (5)
C5—C6—C7—C21.1 (5)C34—C35—C36—C311.0 (5)
C3—C2—C7—C6−3.6 (5)C32—C31—C36—C35−2.2 (5)
C1—C2—C7—C6177.3 (3)C30—C31—C36—C35176.6 (3)
N1—N2—C8—C10−179.5 (3)N3—N4—C37—C39178.8 (3)
Sn1—N2—C8—C100.9 (5)Sn2—N4—C37—C39−0.6 (5)
N1—N2—C8—C90.6 (4)N3—N4—C37—C38−3.0 (5)
Sn1—N2—C8—C9−179.0 (2)Sn2—N4—C37—C38177.6 (2)
N2—C8—C10—C1111.6 (6)N4—C37—C39—C40−14.5 (6)
C9—C8—C10—C11−168.6 (3)C38—C37—C39—C40167.2 (3)
Sn1—O3—C11—C10−29.6 (4)Sn2—O6—C40—C3934.4 (4)
Sn1—O3—C11—C12153.2 (2)Sn2—O6—C40—C41−146.4 (2)
C8—C10—C11—O33.7 (6)C37—C39—C40—O6−3.5 (6)
C8—C10—C11—C12−179.3 (3)C37—C39—C40—C41177.4 (3)
O3—C11—C12—C1718.9 (5)O6—C40—C41—C46−27.2 (4)
C10—C11—C12—C17−158.4 (3)C39—C40—C41—C46152.0 (3)
O3—C11—C12—C13−159.6 (3)O6—C40—C41—C42150.4 (3)
C10—C11—C12—C1323.0 (5)C39—C40—C41—C42−30.4 (5)
C17—C12—C13—C142.5 (6)C46—C41—C42—C43−0.5 (5)
C11—C12—C13—C14−178.9 (3)C40—C41—C42—C43−178.2 (3)
C12—C13—C14—C15−0.7 (6)C41—C42—C43—C440.3 (6)
C13—C14—C15—C16−1.1 (7)C42—C43—C44—C45−0.1 (6)
C14—C15—C16—C171.2 (8)C43—C44—C45—C460.0 (6)
C15—C16—C17—C120.5 (7)C42—C41—C46—C450.5 (5)
C13—C12—C17—C16−2.3 (6)C40—C41—C46—C45178.1 (3)
C11—C12—C17—C16179.0 (4)C44—C45—C46—C41−0.2 (6)
O3—Sn1—C18—C2314.1 (3)O6—Sn2—C47—C488.8 (3)
C24—Sn1—C18—C23−82.7 (3)C53—Sn2—C47—C48−93.6 (3)
O1—Sn1—C18—C23174.9 (3)O4—Sn2—C47—C48167.8 (3)
N2—Sn1—C18—C2399.6 (3)N4—Sn2—C47—C4894.5 (3)
O3—Sn1—C18—C19−169.4 (3)O6—Sn2—C47—C52−171.1 (3)
C24—Sn1—C18—C1993.9 (3)C53—Sn2—C47—C5286.5 (3)
O1—Sn1—C18—C19−8.5 (3)O4—Sn2—C47—C52−12.1 (3)
N2—Sn1—C18—C19−83.8 (3)N4—Sn2—C47—C52−85.4 (3)
C23—C18—C19—C20−0.5 (6)C52—C47—C48—C49−0.9 (5)
Sn1—C18—C19—C20−177.1 (3)Sn2—C47—C48—C49179.2 (3)
C18—C19—C20—C21−0.8 (6)C47—C48—C49—C501.0 (6)
C19—C20—C21—C221.7 (7)C48—C49—C50—C51−0.4 (6)
C20—C21—C22—C23−1.3 (7)C49—C50—C51—C52−0.3 (6)
C21—C22—C23—C180.0 (7)C50—C51—C52—C470.3 (6)
C19—C18—C23—C220.9 (6)C48—C47—C52—C510.3 (5)
Sn1—C18—C23—C22177.5 (3)Sn2—C47—C52—C51−179.8 (3)
O3—Sn1—C24—C25−18.0 (3)O6—Sn2—C53—C548.4 (3)
C18—Sn1—C24—C2579.3 (4)C47—Sn2—C53—C54110.1 (3)
O1—Sn1—C24—C25−178.1 (3)O4—Sn2—C53—C54−150.9 (3)
N2—Sn1—C24—C25−103.3 (3)N4—Sn2—C53—C54−77.1 (3)
O3—Sn1—C24—C29163.2 (3)O6—Sn2—C53—C58−178.1 (3)
C18—Sn1—C24—C29−99.5 (3)C47—Sn2—C53—C58−76.5 (3)
O1—Sn1—C24—C293.1 (3)O4—Sn2—C53—C5822.6 (3)
N2—Sn1—C24—C2977.9 (3)N4—Sn2—C53—C5896.3 (3)
C29—C24—C25—C260.1 (7)C58—C53—C54—C55−2.2 (6)
Sn1—C24—C25—C26−178.7 (4)Sn2—C53—C54—C55171.3 (3)
C24—C25—C26—C271.0 (8)C53—C54—C55—C561.5 (7)
C25—C26—C27—C28−2.2 (8)C54—C55—C56—C570.0 (7)
C26—C27—C28—C292.1 (7)C55—C56—C57—C58−0.8 (6)
C25—C24—C29—C28−0.2 (6)C56—C57—C58—C530.1 (6)
Sn1—C24—C29—C28178.5 (3)C54—C53—C58—C571.4 (6)
C27—C28—C29—C24−0.9 (6)Sn2—C53—C58—C57−172.2 (3)
Cg1, Cg2 and Cg3 are the centroids of the C31–C36, C18–C23 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O2—H2o···O8i0.841.812.650 (4)175
O5—H5o···O7ii0.841.852.681 (4)170
O7—H7o···N3iii0.842.022.830 (4)163
O8—H8o···N1iv0.841.982.821 (4)175
C50—H50···Cg1v0.952.913.440 (5)116
C57—H57···Cg20.952.843.664 (4)145
C60—H60a···Cg3vi0.982.983.886 (6)155
Table 1

Selected bond lengths (Å)

Sn1—O12.124 (2)
Sn1—O32.102 (2)
Sn1—N22.133 (2)
Sn1—C182.118 (4)
Sn1—C242.117 (3)
Sn2—O42.123 (2)
Sn2—O62.094 (2)
Sn2—N42.141 (3)
Sn2—C472.116 (3)
Sn2—C532.124 (3)
Table 2

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C31–C36, C18–C23 and C12–C17 rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
O2—H2o⋯O8i0.841.812.650 (4)175
O5—H5o⋯O7ii0.841.852.681 (4)170
O7—H7o⋯N3iii0.842.022.830 (4)163
O8—H8o⋯N1iv0.841.982.821 (4)175
C50—H50⋯Cg1v0.952.913.440 (5)116
C57—H57⋯Cg20.952.843.664 (4)145
C60—H60a⋯Cg3vi0.982.983.886 (6)155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  5 in total

1.  Qmol: a program for molecular visualization on Windows-based PCs.

Authors:  J D Gans; D Shalloway
Journal:  J Mol Graph Model       Date:  2001       Impact factor: 2.518

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  {4-Hy-droxy-N'-[(2-oxido-1-naphthyl-κO)methyl-idene]benzohydrazidato-κN',O}dimethyl-tin(IV).

Authors:  Md Abu Affan; Norrihan B Sam; Fasihuddin B Ahmad; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-14

4.  {4-Hy-droxy-N'-[(2E,3Z)-4-oxido-4-phenyl-but-3-en-2-yl-idene]benzo-hydrazidato}dimethyl-tin(IV).

Authors:  Md Abu Affan; Norrihan B Sam; Fasihuddin B Ahmad; Fraser White; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-22

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  {4-Hy-droxy-N'-[(2E,3Z)-4-oxido-4-phenyl-but-3-en-2-yl-idene]benzo-hydrazidato}dimethyl-tin(IV).

Authors:  Md Abu Affan; Norrihan B Sam; Fasihuddin B Ahmad; Fraser White; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-22
  1 in total

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