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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m618–m619.
Published online 2010 May 8. doi:  10.1107/S1600536810016016
PMCID: PMC2979428

Di-n-but­yl{1-[1-(2-hydroxy­phen­yl)ethyl­idene]-5-[1-(2-oxidophen­yl)ethyl­idene]thio­carbazonato-κ3 O 5,N 5,S}tin(IV)

Abstract

The ‘symmetrical’ 1,5-bis­[1-(2-hydroxy­phen­yl)ethyl­idene]thio­carbazone Schiff base condenses with dibutyl­tin oxide to form the title complex, [Sn(C4H9)2(C17H16N4O2S)], in which the deprotonated ligand O,N,S-chelates to the Sn atom of two crystallographically independent mol­ecules. The ligand bears a formal negative charge on the S and one O atom; the other O atom retains its H atom. The Sn atoms are five-coordinated in a cis-C2NOSSn trigonal-bipyramidal environment, and the apical sites are occupied by the O and S atoms. In both mol­ecules, the hydr­oxy group is hydrogen bonded to a double-bonded N atom, generating a six-membered ring. The amino group is a donor to the coordinated O atom of an adjacent mol­ecule, the hydrogen-bonding inter­action giving rise to a helical chain running along the b axis. In one of the independent mol­ecules, the atoms of one of the n-butyl groups are disordered over two sets of sites with equal occupancy. In the other independent mol­ecule, the atoms of both n-butyl groups are disordered over two sets of sites with equal occupancy and, in addition, the Sn and S atoms were also refined as disordered over two sets of sites with equal occupancy.

Related literature

For the synthesis of 1,5-bis­(2-hydroxy­benzaldehyde) dithio­carbohydrazone, see: Ren et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m618-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C17H16N4O2S)]
  • M r = 573.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m618-efi1.jpg
  • a = 24.8858 (17) Å
  • b = 9.4528 (7) Å
  • c = 23.6254 (17) Å
  • β = 112.756 (1)°
  • V = 5125.0 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.11 mm−1
  • T = 100 K
  • 0.36 × 0.08 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan SADABS (Sheldrick, 1996 [triangle]) T min = 0.691, T max = 0.917
  • 47957 measured reflections
  • 11772 independent reflections
  • 7256 reflections with I > 2σ(I)
  • R int = 0.076

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.172
  • S = 1.12
  • 11772 reflections
  • 607 parameters
  • 161 restraints
  • H-atom parameters constrained
  • Δρmax = 1.77 e Å−3
  • Δρmin = −1.75 e Å−3

Data collection: APEX2 software (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016016/lh5030sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016016/lh5030Isup2.hkl

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

Acknowledgments

We thank MOSTI (grant No. 06-01-09-SF0046), Universiti Malaysia Sarawak and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

There are many crystallographic studies on metal derivatives of the Schiff bases derived by condensing salicyldehyde (and acetophenone) with semithiocarbazide (and thiocarbazide). 1,5-Bis(2-hydroxyacetophenone) thiocarbazone is a 'symmetrical' ligand; however, in the title di-n-butyltin derivative (Scheme I, Fig. 1), the doubly-deprotonated ligand chelates in a O,N,S-manner and only part of the molecule is used in coordination. There are two independent molecules. The tin atoms are five coordinate in a cis-C2NOSSn trigonal bipyramidal environment, and the apical sites are occupied by the oxgen and sulfur atoms. The hydroxy group is hydrogen bonded to a double-bond nitrogen atom to generate a six-membered ring.

Experimental

1,5-Bis(2-hydroxyacetophenone) thiocarbazone was synthesized by using a literature method (Ren et al., 1999). The compound (0.66 g, 2 mmole) was dissolved in methanol (20 ml). Potassium hydroxide (0.23 g, 4 mmol) dissolved in methanol (5 ml) was added. The orange solution was then treated with di-n-butyltin dichloride (0.61 g, 2 mmol) in methanol (10 ml). The mixture was heated for an hour. The solution was filtered. The evaporation of the solvent gave a product that was recrystallized from ethanol in 60% yield; m.p. 401-403 K.

Refinement

Hydrogen atoms were placed in calculated positions (C—H 0.93 to 0.97, N–H 0.86, O–H 0.824 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C,N,O).

All aromatic rings were refined as rigid hexagons of 1.39 Å sides. Three of the four n-butyl chains were refined as two chains of 0.5 occupancy. The 1,2-related distances were restrained to 1.500±0.005 Å and the 1,3-related ones to 2.350±0.005 Å; tight restraints were used, which led to a somewhat large weighting scheme. The temperature factors of the primed atoms were set to those of the unprimed one; the anisotropic temperature factors of the carbon atoms of the chains were restrained to be nearly isotropic.

The Sn1 atom is disordered with respect to Sn1' and the S1 with respect to S1'. Their occupancies were assumed to be 0.5. The anisotropic temperature factors of these four atoms were also restrained to be nearly isotropic. Additionally, the tin–element and tin-elementprimed distances were restrained to within 0.01 Å of each other. The final difference Fourier map had a peak in the vicinity of the butyl chain belonging to Sn2, and a deep hole in the vicinity of the Sn1/Sn1' atoms.

Some 161 restraints were used to treat the disorder.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of one molecule of Sn(C4H9)2(C17H16N4O2S) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
Fig. 2.
Thermal ellipsoid plot (Barbour, 2001) of second molecule of Sn(C4H9)2(C17H16N4O2S) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is is not shown.

Crystal data

[Sn(C4H9)2(C17H16N4O2S)]F(000) = 2352
Mr = 573.31Dx = 1.486 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5611 reflections
a = 24.8858 (17) Åθ = 2.4–24.0°
b = 9.4528 (7) ŵ = 1.11 mm1
c = 23.6254 (17) ÅT = 100 K
β = 112.756 (1)°Prism, yellow
V = 5125.0 (6) Å30.36 × 0.08 × 0.08 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer11772 independent reflections
Radiation source: fine-focus sealed tube7256 reflections with I > 2σ(I)
graphiteRint = 0.076
ω scansθmax = 27.5°, θmin = 0.9°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)h = −31→32
Tmin = 0.691, Tmax = 0.917k = −12→12
47957 measured reflectionsl = −30→30

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.12w = 1/[σ2(Fo2) + (0.07P)2 + 7.0P] where P = (Fo2 + 2Fc2)/3
11772 reflections(Δ/σ)max = 0.001
607 parametersΔρmax = 1.77 e Å3
161 restraintsΔρmin = −1.74 e Å3

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

xyzUiso*/UeqOcc. (<1)
Sn10.08315 (15)0.8786 (4)0.24832 (18)0.0284 (5)0.50
S1−0.00074 (19)1.0465 (5)0.2565 (2)0.0426 (12)0.50
Sn1'0.08934 (17)0.8945 (4)0.26029 (18)0.0399 (9)0.50
S1'−0.00646 (18)1.0232 (6)0.22995 (18)0.0338 (10)0.50
Sn20.415838 (18)0.26489 (5)0.24037 (2)0.03526 (14)
S20.49991 (7)0.40121 (18)0.23013 (7)0.0373 (4)
O10.14093 (17)0.7062 (4)0.28324 (19)0.0347 (10)
O2−0.0644 (2)0.6440 (7)0.3897 (3)0.081 (2)
H2−0.06420.69490.36070.122*
O30.37888 (18)0.0927 (5)0.27034 (19)0.0386 (10)
O40.6688 (2)0.0452 (6)0.4066 (3)0.0626 (15)
H40.64790.09470.37670.094*
N10.06312 (19)0.8155 (5)0.3305 (2)0.0322 (12)
N20.00592 (19)0.8274 (5)0.3265 (2)0.0329 (12)
N3−0.0824 (2)0.9342 (6)0.2810 (3)0.0489 (16)
H3−0.10570.99480.25650.059*
N4−0.0999 (2)0.8458 (6)0.3160 (3)0.0377 (13)
N50.4907 (2)0.2071 (5)0.3249 (2)0.0307 (11)
N60.5474 (2)0.2214 (5)0.3277 (2)0.0329 (11)
N70.6083 (2)0.3211 (6)0.2874 (2)0.0384 (13)
H70.61510.37660.26210.046*
N80.6519 (2)0.2451 (6)0.3305 (2)0.0389 (13)
C10.0578 (5)0.7902 (16)0.1571 (5)0.040 (2)0.50
H1A0.08260.83300.13750.048*0.50
H1B0.06620.68750.16120.048*0.50
C2−0.0047 (5)0.8099 (15)0.1150 (6)0.058 (3)0.50
H2A−0.03030.76130.13200.070*0.50
H2B−0.01450.91180.11110.070*0.50
C3−0.0139 (7)0.7497 (15)0.0534 (5)0.074 (4)0.50
H3A0.02030.76840.04290.088*0.50
H3B−0.04880.79180.02130.088*0.50
C4−0.0219 (9)0.5939 (14)0.0588 (9)0.074 (4)0.50
H4A−0.03150.54900.01870.111*0.50
H4B−0.05380.57780.07280.111*0.50
H4C0.01410.55290.08850.111*0.50
C50.1541 (7)1.0249 (16)0.2874 (9)0.040 (3)0.50
H5A0.18350.97670.32330.048*0.50
H5B0.17191.03670.25680.048*0.50
C60.1469 (8)1.1705 (13)0.3084 (5)0.058 (3)0.50
H6A0.17861.23330.30820.069*0.50
H6B0.10911.21150.28120.069*0.50
C70.1491 (7)1.1536 (14)0.3721 (5)0.043 (2)0.50
H7A0.18451.10100.39810.051*0.50
H7B0.11431.10300.37200.051*0.50
C80.1507 (13)1.3038 (19)0.3944 (10)0.109 (6)0.50
H8A0.12531.36330.36070.164*0.50
H8B0.19071.33980.40890.164*0.50
H8C0.13701.30590.42820.164*0.50
C1'0.0360 (5)0.8300 (15)0.1686 (5)0.040 (2)0.50
H1'A0.00800.75670.16980.048*0.50
H1'B0.01360.91190.14510.048*0.50
C2'0.0737 (4)0.7725 (17)0.1381 (5)0.058 (3)0.50
H2'A0.08830.67750.15450.070*0.50
H2'B0.10740.83560.14530.070*0.50
C3'0.0365 (6)0.7643 (16)0.0711 (5)0.074 (4)0.50
H3'A0.06070.74210.04740.088*0.50
H3'B0.01650.85560.05640.088*0.50
C4'−0.0071 (8)0.649 (2)0.0634 (9)0.074 (4)0.50
H4'A0.01290.55790.07350.111*0.50
H4'B−0.03540.64800.02080.111*0.50
H4'C−0.02750.66680.09090.111*0.50
C5'0.1531 (7)1.0614 (18)0.2951 (9)0.040 (3)0.50
H5'A0.19281.02070.31320.048*0.50
H5'B0.15121.12590.26140.048*0.50
C6'0.1398 (6)1.1410 (16)0.3431 (7)0.058 (3)0.50
H6'A0.10051.18350.32510.069*0.50
H6'B0.14141.07690.37680.069*0.50
C7'0.1851 (5)1.2537 (12)0.3665 (5)0.043 (2)0.50
H7'A0.18461.31470.33220.051*0.50
H7'B0.22421.21070.38590.051*0.50
C8'0.1714 (11)1.339 (2)0.4125 (11)0.109 (6)0.50
H8'A0.19101.43110.41810.164*0.50
H8'B0.18501.28890.45180.164*0.50
H8'C0.12921.35390.39790.164*0.50
C90.17920 (14)0.7085 (4)0.34316 (13)0.0325 (14)
C100.23793 (15)0.6870 (5)0.35552 (15)0.0404 (16)
H100.25030.66950.32280.048*
C110.27852 (11)0.6910 (5)0.41569 (18)0.0450 (17)
H110.31870.67630.42410.054*
C120.26040 (14)0.7167 (5)0.46350 (13)0.0414 (16)
H120.28810.71950.50460.050*
C130.20168 (15)0.7382 (4)0.45114 (14)0.0361 (14)
H130.18930.75570.48380.043*
C140.16108 (11)0.7342 (4)0.39097 (17)0.0288 (13)
C150.0988 (2)0.7536 (6)0.3813 (3)0.0304 (13)
C160.0769 (3)0.7063 (9)0.4279 (3)0.0474 (18)
H16A0.04280.64550.40860.071*
H16B0.06590.78890.44620.071*
H16C0.10750.65310.46000.071*
C17−0.0251 (3)0.9210 (7)0.2872 (3)0.0446 (17)
C18−0.1529 (3)0.8398 (7)0.3132 (3)0.0374 (15)
C19−0.2014 (3)0.9299 (9)0.2714 (3)0.0506 (19)
H19A−0.18600.99580.24930.076*
H19B−0.21870.98350.29560.076*
H19C−0.23110.86970.24190.076*
C20−0.16271 (19)0.7323 (5)0.35400 (19)0.0415 (16)
C21−0.21728 (16)0.7248 (5)0.3571 (2)0.055 (2)
H21−0.24800.78410.33180.066*
C22−0.22697 (16)0.6304 (6)0.3973 (2)0.058 (2)
H22−0.26430.62520.39940.070*
C23−0.1821 (2)0.5435 (5)0.4344 (2)0.061 (2)
H23−0.18870.47900.46180.073*
C24−0.12750 (19)0.5510 (6)0.4313 (2)0.074 (3)
H24−0.09680.49170.45660.088*
C25−0.11782 (15)0.6454 (6)0.3911 (2)0.054 (2)
C260.3748 (3)0.4348 (7)0.2710 (3)0.0497 (19)
H26A0.35170.49320.23510.060*
H26B0.34750.39280.28760.060*
C270.4165 (3)0.5295 (6)0.3191 (3)0.0500 (18)
H27A0.44300.47140.35340.060*
H27B0.44050.58290.30130.060*
C280.3840 (3)0.6298 (7)0.3425 (3)0.056 (2)
H28A0.36150.57650.36200.067*
H28B0.35620.68490.30790.067*
C290.4256 (3)0.7286 (7)0.3884 (4)0.065 (2)
H29A0.40350.79800.40160.097*
H29B0.44920.77780.36960.097*
H29C0.45110.67450.42400.097*
C300.3902 (8)0.156 (2)0.1545 (6)0.046 (4)0.50
H30A0.37660.06150.16130.055*0.50
H30B0.35540.20640.12600.055*0.50
C310.4281 (9)0.131 (4)0.1196 (12)0.069 (4)0.50
H31A0.46360.07820.14500.082*0.50
H31B0.43970.22170.10690.082*0.50
C320.3920 (7)0.045 (2)0.0644 (7)0.062 (4)0.50
H32A0.3763−0.04020.07680.075*0.50
H32B0.35900.10210.03620.075*0.50
C330.4330 (8)0.006 (3)0.0343 (9)0.062 (4)0.50
H33A0.44530.09130.01920.093*0.50
H33B0.4133−0.0583−0.00010.093*0.50
H33C0.4672−0.04160.06420.093*0.50
C30'0.3751 (8)0.190 (2)0.1485 (5)0.046 (4)0.50
H30C0.35030.10790.14880.055*0.50
H30D0.34890.26490.12370.055*0.50
C31'0.4132 (7)0.145 (4)0.1161 (11)0.069 (4)0.50
H31C0.44000.06870.13920.082*0.50
H31D0.43670.22590.11190.082*0.50
C32'0.3732 (7)0.093 (2)0.0540 (6)0.062 (4)0.50
H32C0.34480.02410.05760.075*0.50
H32D0.35180.17250.02770.075*0.50
C33'0.4133 (8)0.024 (3)0.0284 (9)0.062 (4)0.50
H33D0.44100.09390.02520.093*0.50
H33E0.3904−0.0147−0.01230.093*0.50
H33F0.4347−0.05300.05570.093*0.50
C340.37953 (19)0.1006 (5)0.32815 (15)0.0406 (16)
C350.32778 (16)0.0736 (6)0.33568 (18)0.0531 (19)
H350.29340.05200.30100.064*
C360.32637 (18)0.0782 (6)0.3939 (2)0.061 (2)
H360.29100.05980.39900.073*
C370.3767 (2)0.1099 (6)0.44458 (17)0.060 (2)
H370.37570.11300.48440.072*
C380.42845 (18)0.1369 (5)0.43705 (16)0.0480 (18)
H380.46290.15850.47170.058*
C390.42986 (15)0.1322 (5)0.37884 (19)0.0393 (15)
C400.4869 (3)0.1524 (7)0.3742 (3)0.0369 (15)
C410.5422 (3)0.1093 (7)0.4265 (3)0.0466 (17)
H41A0.56470.04590.41110.070*
H41B0.53260.06030.45780.070*
H41C0.56550.19370.44440.070*
C420.5535 (3)0.3044 (7)0.2865 (3)0.0337 (14)
C430.7052 (3)0.2502 (7)0.3353 (3)0.0418 (16)
C440.7260 (3)0.3415 (9)0.2964 (4)0.057 (2)
H44A0.69280.39140.26610.086*
H44B0.74470.28250.27520.086*
H44C0.75410.41040.32240.086*
C450.74599 (18)0.1546 (5)0.3824 (2)0.053 (2)
C460.8050 (2)0.1596 (5)0.3932 (2)0.062 (2)
H460.81880.22610.37180.075*
C470.84367 (15)0.0674 (6)0.4351 (3)0.086 (4)
H470.88400.07090.44240.103*
C480.8234 (2)−0.0299 (5)0.4664 (2)0.088 (4)
H480.8499−0.09290.49500.106*
C490.7645 (2)−0.0350 (5)0.4556 (2)0.084 (3)
H490.7506−0.10150.47700.100*
C500.72574 (16)0.0572 (5)0.4137 (2)0.061 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0098 (8)0.0273 (8)0.0387 (13)−0.0062 (7)−0.0008 (10)0.0071 (8)
S10.0235 (17)0.036 (2)0.051 (3)−0.0030 (15)−0.005 (2)0.024 (2)
Sn1'0.0187 (9)0.0377 (13)0.0429 (15)−0.0142 (7)−0.0107 (8)0.0185 (11)
S1'0.0245 (18)0.048 (2)0.029 (2)0.0103 (16)0.0105 (17)0.0170 (19)
Sn20.0277 (2)0.0409 (3)0.0404 (3)0.00486 (19)0.01672 (19)0.0118 (2)
S20.0295 (8)0.0448 (10)0.0408 (9)0.0037 (7)0.0172 (7)0.0121 (7)
O10.021 (2)0.042 (3)0.037 (2)−0.0012 (18)0.0068 (18)0.0036 (19)
O20.042 (3)0.093 (5)0.131 (6)0.032 (3)0.057 (4)0.058 (4)
O30.036 (2)0.045 (3)0.042 (2)−0.001 (2)0.022 (2)0.008 (2)
O40.047 (3)0.043 (3)0.073 (4)−0.008 (2)−0.005 (3)0.005 (3)
N10.013 (2)0.025 (3)0.052 (3)0.0000 (19)0.005 (2)0.003 (2)
N20.015 (2)0.029 (3)0.050 (3)0.000 (2)0.007 (2)0.003 (2)
N30.017 (2)0.040 (3)0.082 (4)0.003 (2)0.011 (3)0.018 (3)
N40.020 (2)0.034 (3)0.057 (3)−0.003 (2)0.013 (2)−0.007 (3)
N50.034 (3)0.024 (3)0.038 (3)0.004 (2)0.019 (2)0.002 (2)
N60.028 (3)0.033 (3)0.034 (3)0.003 (2)0.009 (2)−0.004 (2)
N70.031 (3)0.049 (3)0.035 (3)−0.005 (3)0.012 (2)−0.001 (2)
N80.031 (3)0.038 (3)0.038 (3)−0.002 (2)0.002 (2)−0.010 (2)
C10.039 (6)0.037 (5)0.047 (5)0.014 (4)0.021 (4)−0.008 (4)
C20.035 (5)0.064 (6)0.057 (6)0.005 (5)−0.002 (4)−0.014 (5)
C30.058 (6)0.075 (7)0.081 (7)0.006 (6)0.020 (6)0.012 (6)
C40.049 (7)0.080 (9)0.077 (6)−0.025 (7)0.008 (6)−0.024 (7)
C50.037 (4)0.013 (7)0.056 (5)−0.009 (4)0.001 (3)0.013 (4)
C60.061 (6)0.050 (6)0.063 (7)0.004 (5)0.024 (6)−0.005 (6)
C70.037 (5)0.040 (5)0.049 (5)−0.002 (4)0.014 (4)0.007 (4)
C80.121 (11)0.098 (9)0.118 (10)0.016 (8)0.056 (8)−0.013 (7)
C1'0.039 (6)0.037 (5)0.047 (5)0.014 (4)0.021 (4)−0.008 (4)
C2'0.035 (5)0.064 (6)0.057 (6)0.005 (5)−0.002 (4)−0.014 (5)
C3'0.058 (6)0.075 (7)0.081 (7)0.006 (6)0.020 (6)0.012 (6)
C4'0.049 (7)0.080 (9)0.077 (6)−0.025 (7)0.008 (6)−0.024 (7)
C5'0.037 (4)0.013 (7)0.056 (5)−0.009 (4)0.001 (3)0.013 (4)
C6'0.061 (6)0.050 (6)0.063 (7)0.004 (5)0.024 (6)−0.005 (6)
C7'0.037 (5)0.040 (5)0.049 (5)−0.002 (4)0.014 (4)0.007 (4)
C8'0.121 (11)0.098 (9)0.118 (10)0.016 (8)0.056 (8)−0.013 (7)
C90.023 (3)0.028 (3)0.042 (3)−0.005 (2)0.008 (3)0.007 (3)
C100.027 (3)0.051 (4)0.041 (4)−0.002 (3)0.011 (3)0.005 (3)
C110.018 (3)0.060 (5)0.054 (4)0.003 (3)0.011 (3)0.007 (3)
C120.023 (3)0.054 (4)0.041 (4)−0.002 (3)0.006 (3)0.005 (3)
C130.026 (3)0.039 (4)0.042 (3)0.001 (3)0.013 (3)0.001 (3)
C140.021 (3)0.019 (3)0.043 (3)−0.006 (2)0.009 (2)0.002 (2)
C150.022 (3)0.022 (3)0.042 (3)−0.003 (2)0.006 (2)−0.002 (3)
C160.026 (3)0.074 (5)0.040 (4)−0.003 (3)0.011 (3)0.005 (4)
C170.017 (3)0.036 (4)0.072 (5)−0.001 (3)0.008 (3)0.008 (3)
C180.024 (3)0.045 (4)0.042 (4)−0.001 (3)0.011 (3)−0.014 (3)
C190.024 (3)0.078 (5)0.047 (4)0.010 (3)0.011 (3)−0.006 (4)
C200.031 (3)0.051 (4)0.044 (4)−0.008 (3)0.016 (3)−0.021 (3)
C210.031 (4)0.088 (6)0.049 (4)−0.007 (4)0.018 (3)−0.009 (4)
C220.038 (4)0.081 (6)0.066 (5)−0.011 (4)0.032 (4)−0.026 (5)
C230.054 (5)0.082 (6)0.062 (5)−0.002 (4)0.039 (4)−0.007 (4)
C240.051 (5)0.099 (7)0.089 (6)0.019 (5)0.047 (5)0.031 (6)
C250.040 (4)0.064 (5)0.068 (5)0.012 (4)0.032 (4)0.002 (4)
C260.043 (4)0.056 (4)0.063 (4)0.025 (3)0.035 (3)0.027 (4)
C270.045 (4)0.040 (4)0.075 (5)0.009 (3)0.035 (4)0.009 (3)
C280.059 (4)0.056 (4)0.067 (5)0.016 (4)0.040 (4)0.018 (4)
C290.079 (5)0.050 (5)0.090 (6)0.010 (4)0.060 (5)0.008 (4)
C300.038 (8)0.058 (8)0.032 (4)−0.008 (6)0.001 (4)0.015 (5)
C310.071 (8)0.074 (7)0.073 (6)−0.025 (8)0.042 (6)−0.014 (5)
C320.065 (8)0.062 (9)0.069 (6)−0.021 (7)0.037 (6)−0.019 (6)
C330.059 (10)0.056 (7)0.051 (5)−0.003 (8)0.000 (7)−0.011 (5)
C30'0.038 (8)0.058 (8)0.032 (4)−0.008 (6)0.001 (4)0.015 (5)
C31'0.071 (8)0.074 (7)0.073 (6)−0.025 (8)0.042 (6)−0.014 (5)
C32'0.065 (8)0.062 (9)0.069 (6)−0.021 (7)0.037 (6)−0.019 (6)
C33'0.059 (10)0.056 (7)0.051 (5)−0.003 (8)0.000 (7)−0.011 (5)
C340.046 (4)0.037 (4)0.046 (4)0.005 (3)0.026 (3)0.010 (3)
C350.052 (4)0.063 (5)0.056 (5)0.001 (4)0.034 (4)0.005 (4)
C360.062 (5)0.073 (6)0.066 (5)−0.005 (4)0.044 (5)0.003 (4)
C370.074 (6)0.068 (6)0.058 (5)0.001 (5)0.047 (5)0.006 (4)
C380.066 (5)0.034 (4)0.049 (4)0.007 (4)0.028 (4)0.004 (3)
C390.052 (4)0.026 (3)0.047 (4)0.002 (3)0.028 (3)0.002 (3)
C400.049 (4)0.028 (3)0.036 (3)0.003 (3)0.019 (3)0.004 (3)
C410.060 (5)0.042 (4)0.037 (4)0.008 (3)0.017 (3)0.010 (3)
C420.032 (3)0.037 (4)0.034 (3)0.004 (3)0.015 (3)−0.001 (3)
C430.032 (3)0.042 (4)0.045 (4)−0.009 (3)0.008 (3)−0.021 (3)
C440.025 (3)0.080 (6)0.061 (5)−0.008 (4)0.010 (3)−0.022 (4)
C450.032 (4)0.036 (4)0.069 (5)0.003 (3)−0.005 (3)−0.028 (4)
C460.034 (4)0.063 (5)0.070 (5)−0.002 (4)−0.002 (4)−0.034 (4)
C470.036 (4)0.066 (6)0.110 (8)0.013 (4)−0.023 (5)−0.047 (6)
C480.060 (6)0.047 (5)0.101 (8)0.014 (5)−0.029 (5)−0.026 (5)
C490.053 (5)0.045 (5)0.106 (7)0.002 (4)−0.021 (5)−0.007 (5)
C500.038 (4)0.035 (4)0.077 (6)−0.003 (3)−0.014 (4)−0.016 (4)

Geometric parameters (Å, °)

Sn1—O12.118 (5)C11—H110.9500
Sn1—C52.150 (9)C12—C131.3900
Sn1—C12.165 (9)C12—H120.9500
Sn1—N12.264 (6)C13—C141.3900
Sn1—S12.689 (5)C13—H130.9500
S1—C171.625 (8)C14—C151.489 (6)
Sn1'—O12.138 (5)C15—C161.473 (9)
Sn1'—N12.139 (7)C16—H16A0.9800
Sn1'—C1'2.145 (9)C16—H16B0.9800
Sn1'—C5'2.161 (8)C16—H16C0.9800
Sn1'—S1'2.521 (5)C18—C201.484 (8)
S1'—C171.862 (8)C18—C191.495 (9)
Sn2—O32.122 (4)C19—H19A0.9800
Sn2—C30'2.132 (8)C19—H19B0.9800
Sn2—C302.140 (8)C19—H19C0.9800
Sn2—C262.172 (6)C20—C211.3900
Sn2—N52.209 (5)C20—C251.3900
Sn2—S22.5470 (16)C21—C221.3900
S2—C421.736 (6)C21—H210.9500
O1—C91.367 (5)C22—C231.3900
O2—C251.342 (5)C22—H220.9500
O2—H20.8400C23—C241.3900
O3—C341.362 (5)C23—H230.9500
O4—C501.366 (6)C24—C251.3900
O4—H40.8400C24—H240.9500
N1—C151.321 (7)C26—C271.502 (5)
N1—N21.394 (6)C26—H26A0.9900
N2—C171.299 (8)C26—H26B0.9900
N3—N41.358 (8)C27—C281.485 (5)
N3—C171.381 (8)C27—H27A0.9900
N3—H30.8600C27—H27B0.9900
N4—C181.297 (8)C28—C291.500 (5)
N5—C401.313 (8)C28—H28A0.9900
N5—N61.393 (7)C28—H28B0.9900
N6—C421.303 (8)C29—H29A0.9800
N7—C421.366 (8)C29—H29B0.9800
N7—N81.370 (7)C29—H29C0.9800
N7—H70.8600C30—C311.492 (5)
N8—C431.288 (8)C30—H30A0.9900
C1—C21.497 (5)C30—H30B0.9900
C1—H1A0.9900C31—C321.500 (5)
C1—H1B0.9900C31—H31A0.9900
C2—C31.494 (5)C31—H31B0.9900
C2—H2A0.9900C32—C331.500 (5)
C2—H2B0.9900C32—H32A0.9900
C3—C41.499 (5)C32—H32B0.9900
C3—H3A0.9900C33—H33A0.9800
C3—H3B0.9900C33—H33B0.9800
C4—H4A0.9800C33—H33C0.9800
C4—H4B0.9800C30'—C31'1.491 (5)
C4—H4C0.9800C30'—H30C0.9900
C5—C61.497 (5)C30'—H30D0.9900
C5—H5A0.9900C31'—C32'1.502 (5)
C5—H5B0.9900C31'—H31C0.9900
C6—C71.492 (5)C31'—H31D0.9900
C6—H6A0.9900C32'—C33'1.501 (5)
C6—H6B0.9900C32'—H32C0.9900
C7—C81.511 (5)C32'—H32D0.9900
C7—H7A0.9900C33'—H33D0.9800
C7—H7B0.9900C33'—H33E0.9800
C8—H8A0.9800C33'—H33F0.9800
C8—H8B0.9800C34—C351.3900
C8—H8C0.9800C34—C391.3900
C1'—C2'1.488 (5)C35—C361.3900
C1'—H1'A0.9900C35—H350.9500
C1'—H1'B0.9900C36—C371.3900
C2'—C3'1.495 (5)C36—H360.9500
C2'—H2'A0.9900C37—C381.3900
C2'—H2'B0.9900C37—H370.9500
C3'—C4'1.497 (5)C38—C391.3900
C3'—H3'A0.9900C38—H380.9500
C3'—H3'B0.9900C39—C401.477 (7)
C4'—H4'A0.9800C40—C411.507 (9)
C4'—H4'B0.9800C41—H41A0.9800
C4'—H4'C0.9800C41—H41B0.9800
C5'—C6'1.499 (5)C41—H41C0.9800
C5'—H5'A0.9900C43—C451.488 (8)
C5'—H5'B0.9900C43—C441.489 (10)
C6'—C7'1.492 (5)C44—H44A0.9800
C6'—H6'A0.9900C44—H44B0.9800
C6'—H6'B0.9900C44—H44C0.9800
C7'—C8'1.498 (5)C45—C461.3900
C7'—H7'A0.9900C45—C501.3900
C7'—H7'B0.9900C46—C471.3900
C8'—H8'A0.9800C46—H460.9500
C8'—H8'B0.9800C47—C481.3900
C8'—H8'C0.9800C47—H470.9500
C9—C101.3900C48—C491.3900
C9—C141.3900C48—H480.9500
C10—C111.3900C49—C501.3900
C10—H100.9500C49—H490.9500
C11—C121.3900
O1—Sn1—C590.4 (6)C13—C14—C15117.1 (3)
O1—Sn1—C189.1 (4)C9—C14—C15122.9 (3)
C5—Sn1—C1123.4 (6)N1—C15—C16120.1 (5)
O1—Sn1—N178.7 (2)N1—C15—C14119.2 (5)
C5—Sn1—N1102.6 (5)C16—C15—C14120.8 (5)
C1—Sn1—N1132.5 (5)C15—C16—H16A109.5
O1—Sn1—S1148.8 (2)C15—C16—H16B109.5
C5—Sn1—S196.9 (5)H16A—C16—H16B109.5
C1—Sn1—S1111.3 (4)C15—C16—H16C109.5
N1—Sn1—S170.05 (18)H16A—C16—H16C109.5
C17—S1—Sn192.0 (3)H16B—C16—H16C109.5
O1—Sn1'—N181.1 (2)N2—C17—N3116.2 (6)
O1—Sn1'—C1'95.5 (4)N2—C17—S1126.5 (5)
N1—Sn1'—C1'115.4 (4)N3—C17—S1115.8 (5)
O1—Sn1'—C5'103.4 (6)N2—C17—S1'128.8 (5)
N1—Sn1'—C5'111.0 (5)N3—C17—S1'114.4 (5)
C1'—Sn1'—C5'131.9 (7)N4—C18—C20114.7 (6)
O1—Sn1'—S1'152.0 (3)N4—C18—C19123.6 (6)
N1—Sn1'—S1'81.4 (2)C20—C18—C19121.7 (5)
C1'—Sn1'—S1'72.7 (3)C18—C19—H19A109.5
C5'—Sn1'—S1'103.3 (6)C18—C19—H19B109.5
C17—S1'—Sn1'91.0 (3)H19A—C19—H19B109.5
O3—Sn2—C30'89.3 (7)C18—C19—H19C109.5
O3—Sn2—C3086.5 (7)H19A—C19—H19C109.5
C30'—Sn2—C3012.6 (9)H19B—C19—H19C109.5
O3—Sn2—C2697.8 (2)C21—C20—C25120.0
C30'—Sn2—C26119.2 (5)C21—C20—C18118.6 (4)
C30—Sn2—C26131.7 (5)C25—C20—C18121.3 (4)
O3—Sn2—N580.31 (17)C22—C21—C20120.0
C30'—Sn2—N5137.7 (5)C22—C21—H21120.0
C30—Sn2—N5125.1 (5)C20—C21—H21120.0
C26—Sn2—N5102.9 (2)C21—C22—C23120.0
O3—Sn2—S2153.89 (12)C21—C22—H22120.0
C30'—Sn2—S299.0 (7)C23—C22—H22120.0
C30—Sn2—S296.2 (6)C24—C23—C22120.0
C26—Sn2—S299.59 (18)C24—C23—H23120.0
N5—Sn2—S276.94 (13)C22—C23—H23120.0
C42—S2—Sn294.3 (2)C23—C24—C25120.0
C9—O1—Sn1119.1 (3)C23—C24—H24120.0
C9—O1—Sn1'111.0 (3)C25—C24—H24120.0
C25—O2—H2109.5O2—C25—C24116.4 (4)
C34—O3—Sn2117.0 (3)O2—C25—C20123.6 (4)
C50—O4—H4109.5C24—C25—C20120.0
C15—N1—N2114.0 (5)C27—C26—Sn2114.6 (4)
C15—N1—Sn1'124.1 (4)C27—C26—H26A108.6
N2—N1—Sn1'121.9 (4)Sn2—C26—H26A108.6
C15—N1—Sn1127.1 (4)C27—C26—H26B108.6
N2—N1—Sn1118.6 (4)Sn2—C26—H26B108.6
C17—N2—N1114.4 (5)H26A—C26—H26B107.6
N4—N3—C17116.1 (5)C28—C27—C26110.2 (5)
N4—N3—H3122.0C28—C27—H27A109.6
C17—N3—H3122.0C26—C27—H27A109.6
C18—N4—N3123.7 (6)C28—C27—H27B109.6
C40—N5—N6114.6 (5)C26—C27—H27B109.6
C40—N5—Sn2125.1 (4)H27A—C27—H27B108.1
N6—N5—Sn2120.3 (4)C27—C28—C29110.1 (5)
C42—N6—N5115.4 (5)C27—C28—H28A109.6
C42—N7—N8116.8 (5)C29—C28—H28A109.6
C42—N7—H7121.6C27—C28—H28B109.6
N8—N7—H7121.6C29—C28—H28B109.6
C43—N8—N7122.6 (6)H28A—C28—H28B108.1
C2—C1—Sn1116.2 (8)C28—C29—H29A109.5
C2—C1—H1A108.2C28—C29—H29B109.5
Sn1—C1—H1A108.2H29A—C29—H29B109.5
C2—C1—H1B108.2C28—C29—H29C109.5
Sn1—C1—H1B108.2H29A—C29—H29C109.5
H1A—C1—H1B107.4H29B—C29—H29C109.5
C3—C2—C1109.2 (7)C31—C30—Sn2125.5 (11)
C3—C2—H2A109.8C31—C30—H30A105.9
C1—C2—H2A109.8Sn2—C30—H30A105.9
C3—C2—H2B109.8C31—C30—H30B105.9
C1—C2—H2B109.8Sn2—C30—H30B105.9
H2A—C2—H2B108.3H30A—C30—H30B106.3
C2—C3—C4105.4 (7)C30—C31—C32105.8 (7)
C2—C3—H3A110.7C30—C31—H31A110.6
C4—C3—H3A110.7C32—C31—H31A110.6
C2—C3—H3B110.7C30—C31—H31B110.6
C4—C3—H3B110.7C32—C31—H31B110.6
H3A—C3—H3B108.8H31A—C31—H31B108.7
C3—C4—H4A109.5C33—C32—C31104.9 (7)
C3—C4—H4B109.5C33—C32—H32A110.8
H4A—C4—H4B109.5C31—C32—H32A110.8
C3—C4—H4C109.5C33—C32—H32B110.8
H4A—C4—H4C109.5C31—C32—H32B110.8
H4B—C4—H4C109.5H32A—C32—H32B108.8
C6—C5—Sn1123.4 (11)C32—C33—H33A109.5
C6—C5—H5A106.5C32—C33—H33B109.5
Sn1—C5—H5A106.5H33A—C33—H33B109.5
C6—C5—H5B106.5C32—C33—H33C109.5
Sn1—C5—H5B106.5H33A—C33—H33C109.5
H5A—C5—H5B106.5H33B—C33—H33C109.5
C7—C6—C5105.8 (7)C31'—C30'—Sn2118.1 (10)
C7—C6—H6A110.6C31'—C30'—H30C107.8
C5—C6—H6A110.6Sn2—C30'—H30C107.8
C7—C6—H6B110.6C31'—C30'—H30D107.8
C5—C6—H6B110.6Sn2—C30'—H30D107.8
H6A—C6—H6B108.7H30C—C30'—H30D107.1
C6—C7—C8103.8 (7)C30'—C31'—C32'106.3 (7)
C6—C7—H7A111.0C30'—C31'—H31C110.5
C8—C7—H7A111.0C32'—C31'—H31C110.5
C6—C7—H7B111.0C30'—C31'—H31D110.5
C8—C7—H7B111.0C32'—C31'—H31D110.5
H7A—C7—H7B109.0H31C—C31'—H31D108.7
C7—C8—H8A109.5C33'—C32'—C31'104.1 (7)
C7—C8—H8B109.5C33'—C32'—H32C110.9
H8A—C8—H8B109.5C31'—C32'—H32C110.9
C7—C8—H8C109.5C33'—C32'—H32D110.9
H8A—C8—H8C109.5C31'—C32'—H32D110.9
H8B—C8—H8C109.5H32C—C32'—H32D109.0
C2'—C1'—Sn1'109.5 (7)C32'—C33'—H33D109.5
C2'—C1'—H1'A109.8C32'—C33'—H33E109.5
Sn1'—C1'—H1'A109.8H33D—C33'—H33E109.5
C2'—C1'—H1'B109.8C32'—C33'—H33F109.5
Sn1'—C1'—H1'B109.8H33D—C33'—H33F109.5
H1'A—C1'—H1'B108.2H33E—C33'—H33F109.5
C1'—C2'—C3'106.5 (7)O3—C34—C35117.8 (3)
C1'—C2'—H2'A110.4O3—C34—C39122.2 (3)
C3'—C2'—H2'A110.4C35—C34—C39120.0
C1'—C2'—H2'B110.4C36—C35—C34120.0
C3'—C2'—H2'B110.4C36—C35—H35120.0
H2'A—C2'—H2'B108.6C34—C35—H35120.0
C2'—C3'—C4'106.8 (7)C35—C36—C37120.0
C2'—C3'—H3'A110.4C35—C36—H36120.0
C4'—C3'—H3'A110.4C37—C36—H36120.0
C2'—C3'—H3'B110.4C38—C37—C36120.0
C4'—C3'—H3'B110.4C38—C37—H37120.0
H3'A—C3'—H3'B108.6C36—C37—H37120.0
C3'—C4'—H4'A109.5C37—C38—C39120.0
C3'—C4'—H4'B109.5C37—C38—H38120.0
H4'A—C4'—H4'B109.5C39—C38—H38120.0
C3'—C4'—H4'C109.5C38—C39—C34120.0
H4'A—C4'—H4'C109.5C38—C39—C40117.5 (4)
H4'B—C4'—H4'C109.5C34—C39—C40122.4 (4)
C6'—C5'—Sn1'108.1 (7)N5—C40—C39121.2 (5)
C6'—C5'—H5'A110.1N5—C40—C41118.5 (6)
Sn1'—C5'—H5'A110.1C39—C40—C41120.3 (5)
C6'—C5'—H5'B110.1C40—C41—H41A109.5
Sn1'—C5'—H5'B110.1C40—C41—H41B109.5
H5'A—C5'—H5'B108.4H41A—C41—H41B109.5
C7'—C6'—C5'106.5 (6)C40—C41—H41C109.5
C7'—C6'—H6'A110.4H41A—C41—H41C109.5
C5'—C6'—H6'A110.4H41B—C41—H41C109.5
C7'—C6'—H6'B110.4N6—C42—N7117.5 (6)
C5'—C6'—H6'B110.4N6—C42—S2127.9 (5)
H6'A—C6'—H6'B108.6N7—C42—S2114.6 (5)
C6'—C7'—C8'107.7 (7)N8—C43—C45115.0 (6)
C6'—C7'—H7'A110.2N8—C43—C44124.0 (7)
C8'—C7'—H7'A110.2C45—C43—C44121.0 (6)
C6'—C7'—H7'B110.2C43—C44—H44A109.5
C8'—C7'—H7'B110.2C43—C44—H44B109.5
H7'A—C7'—H7'B108.5H44A—C44—H44B109.5
C7'—C8'—H8'A109.5C43—C44—H44C109.5
C7'—C8'—H8'B109.5H44A—C44—H44C109.5
H8'A—C8'—H8'B109.5H44B—C44—H44C109.5
C7'—C8'—H8'C109.5C46—C45—C50120.0
H8'A—C8'—H8'C109.5C46—C45—C43118.8 (4)
H8'B—C8'—H8'C109.5C50—C45—C43121.2 (4)
O1—C9—C10118.0 (3)C45—C46—C47120.0
O1—C9—C14122.0 (3)C45—C46—H46120.0
C10—C9—C14120.0C47—C46—H46120.0
C11—C10—C9120.0C48—C47—C46120.0
C11—C10—H10120.0C48—C47—H47120.0
C9—C10—H10120.0C46—C47—H47120.0
C10—C11—C12120.0C49—C48—C47120.0
C10—C11—H11120.0C49—C48—H48120.0
C12—C11—H11120.0C47—C48—H48120.0
C11—C12—C13120.0C50—C49—C48120.0
C11—C12—H12120.0C50—C49—H49120.0
C13—C12—H12120.0C48—C49—H49120.0
C12—C13—C14120.0O4—C50—C49115.8 (4)
C12—C13—H13120.0O4—C50—C45124.2 (4)
C14—C13—H13120.0C49—C50—C45120.0
C13—C14—C9120.0
O1—Sn1—S1—C17−29.4 (6)O1—C9—C14—C13−178.8 (4)
C5—Sn1—S1—C17−131.7 (7)C10—C9—C14—C130.0
C1—Sn1—S1—C1798.2 (6)O1—C9—C14—C153.2 (5)
N1—Sn1—S1—C17−30.8 (3)C10—C9—C14—C15−178.0 (4)
O1—Sn1'—S1'—C1744.1 (6)N2—N1—C15—C16−0.9 (8)
N1—Sn1'—S1'—C17−7.9 (3)Sn1'—N1—C15—C16178.2 (5)
C1'—Sn1'—S1'—C17112.2 (5)Sn1—N1—C15—C16−173.7 (5)
C5'—Sn1'—S1'—C17−117.6 (6)N2—N1—C15—C14179.8 (4)
O3—Sn2—S2—C42−14.4 (4)Sn1'—N1—C15—C14−1.1 (7)
C30'—Sn2—S2—C42−121.5 (6)Sn1—N1—C15—C147.0 (8)
C30—Sn2—S2—C42−109.1 (6)C13—C14—C15—N1148.4 (4)
C26—Sn2—S2—C42116.7 (3)C9—C14—C15—N1−33.6 (7)
N5—Sn2—S2—C4215.6 (2)C13—C14—C15—C16−30.9 (7)
C5—Sn1—O1—C947.8 (6)C9—C14—C15—C16147.2 (5)
C1—Sn1—O1—C9171.3 (5)N1—N2—C17—N3178.9 (6)
N1—Sn1—O1—C9−54.9 (4)N1—N2—C17—S1−16.0 (9)
S1—Sn1—O1—C9−56.3 (6)N1—N2—C17—S1'8.2 (9)
C5—Sn1—O1—Sn1'41.1 (15)N4—N3—C17—N2−1.2 (9)
C1—Sn1—O1—Sn1'164.5 (16)N4—N3—C17—S1−168.0 (5)
N1—Sn1—O1—Sn1'−61.6 (14)N4—N3—C17—S1'170.8 (5)
S1—Sn1—O1—Sn1'−63.0 (13)Sn1—S1—C17—N237.7 (7)
N1—Sn1'—O1—C9−61.3 (3)Sn1—S1—C17—N3−157.1 (6)
C1'—Sn1'—O1—C9−176.2 (5)Sn1—S1—C17—S1'−66.5 (7)
C5'—Sn1'—O1—C948.3 (6)Sn1'—S1'—C17—N22.8 (7)
S1'—Sn1'—O1—C9−113.3 (5)Sn1'—S1'—C17—N3−168.0 (5)
N1—Sn1'—O1—Sn1112.4 (15)Sn1'—S1'—C17—S193.5 (7)
C1'—Sn1'—O1—Sn1−2.5 (14)N3—N4—C18—C20178.1 (5)
C5'—Sn1'—O1—Sn1−138.0 (16)N3—N4—C18—C19−0.2 (10)
S1'—Sn1'—O1—Sn160.4 (14)N4—C18—C20—C21175.8 (4)
C30'—Sn2—O3—C34−165.5 (6)C19—C18—C20—C21−5.8 (7)
C30—Sn2—O3—C34−177.8 (6)N4—C18—C20—C25−0.7 (7)
C26—Sn2—O3—C34−46.1 (4)C19—C18—C20—C25177.6 (5)
N5—Sn2—O3—C3455.7 (4)C25—C20—C21—C220.0
S2—Sn2—O3—C3485.3 (4)C18—C20—C21—C22−176.6 (5)
O1—Sn1'—N1—C1538.7 (5)C20—C21—C22—C230.0
C1'—Sn1'—N1—C15130.6 (6)C21—C22—C23—C240.0
C5'—Sn1'—N1—C15−62.3 (8)C22—C23—C24—C250.0
S1'—Sn1'—N1—C15−163.3 (5)C23—C24—C25—O2−178.5 (6)
O1—Sn1'—N1—N2−142.2 (4)C23—C24—C25—C200.0
C1'—Sn1'—N1—N2−50.4 (6)C21—C20—C25—O2178.4 (7)
C5'—Sn1'—N1—N2116.8 (7)C18—C20—C25—O2−5.1 (7)
S1'—Sn1'—N1—N215.8 (4)C21—C20—C25—C240.0
O1—Sn1'—N1—Sn1−78.0 (13)C18—C20—C25—C24176.5 (5)
C1'—Sn1'—N1—Sn113.9 (12)O3—Sn2—C26—C27117.1 (5)
S1'—Sn1'—N1—Sn180.0 (13)C30'—Sn2—C26—C27−149.4 (9)
O1—Sn1—N1—C1527.7 (5)C30—Sn2—C26—C27−150.7 (10)
C5—Sn1—N1—C15−60.1 (7)N5—Sn2—C26—C2735.3 (5)
C1—Sn1—N1—C15105.9 (7)S2—Sn2—C26—C27−43.4 (5)
S1—Sn1—N1—C15−153.0 (5)Sn2—C26—C27—C28−172.8 (5)
O1—Sn1—N1—N2−144.8 (4)C26—C27—C28—C29−177.5 (6)
C5—Sn1—N1—N2127.4 (6)O3—Sn2—C30—C31−132 (3)
C1—Sn1—N1—N2−66.6 (6)C30'—Sn2—C30—C31125 (7)
S1—Sn1—N1—N234.5 (4)C26—Sn2—C30—C31130 (2)
O1—Sn1—N1—Sn1'95.7 (13)N5—Sn2—C30—C31−57 (3)
C5—Sn1—N1—Sn1'7.9 (13)S2—Sn2—C30—C3122 (3)
C1—Sn1—N1—Sn1'173.9 (16)Sn2—C30—C31—C32177.5 (18)
S1—Sn1—N1—Sn1'−85.0 (13)C30—C31—C32—C33−173 (2)
C15—N1—N2—C17161.2 (6)O3—Sn2—C30'—C31'−117 (2)
Sn1'—N1—N2—C17−17.9 (7)C30—Sn2—C30'—C31'−40 (5)
Sn1—N1—N2—C17−25.4 (7)C26—Sn2—C30'—C31'144 (2)
C17—N3—N4—C18−176.3 (6)N5—Sn2—C30'—C31'−43 (3)
O3—Sn2—N5—C40−31.0 (5)S2—Sn2—C30'—C31'38 (2)
C30'—Sn2—N5—C40−109.0 (11)Sn2—C30'—C31'—C32'178.1 (19)
C30—Sn2—N5—C40−109.7 (9)C30'—C31'—C32'—C33'−169 (2)
C26—Sn2—N5—C4064.9 (5)Sn2—O3—C34—C35130.8 (3)
S2—Sn2—N5—C40161.9 (5)Sn2—O3—C34—C39−50.2 (5)
O3—Sn2—N5—N6146.0 (4)O3—C34—C35—C36179.0 (4)
C30'—Sn2—N5—N667.9 (11)C39—C34—C35—C360.0
C30—Sn2—N5—N667.3 (9)C34—C35—C36—C370.0
C26—Sn2—N5—N6−118.2 (4)C35—C36—C37—C380.0
S2—Sn2—N5—N6−21.1 (4)C36—C37—C38—C390.0
C40—N5—N6—C42−164.4 (5)C37—C38—C39—C340.0
Sn2—N5—N6—C4218.4 (7)C37—C38—C39—C40−176.0 (5)
C42—N7—N8—C43178.9 (6)O3—C34—C39—C38−179.0 (5)
O1—Sn1—C1—C2145.0 (12)C35—C34—C39—C380.0
C5—Sn1—C1—C2−125.1 (13)O3—C34—C39—C40−3.2 (5)
N1—Sn1—C1—C271.3 (13)C35—C34—C39—C40175.8 (5)
S1—Sn1—C1—C2−10.7 (13)N6—N5—C40—C39179.1 (5)
Sn1—C1—C2—C3177.0 (9)Sn2—N5—C40—C39−3.8 (8)
C1—C2—C3—C482.0 (15)N6—N5—C40—C41−1.4 (8)
O1—Sn1—C5—C6−150.2 (13)Sn2—N5—C40—C41175.7 (4)
C1—Sn1—C5—C6120.6 (11)C38—C39—C40—N5−151.4 (5)
N1—Sn1—C5—C6−71.7 (14)C34—C39—C40—N532.7 (7)
S1—Sn1—C5—C6−0.7 (13)C38—C39—C40—C4129.1 (7)
Sn1—C5—C6—C784.2 (16)C34—C39—C40—C41−146.9 (5)
C5—C6—C7—C8171.9 (16)N5—N6—C42—N7−179.7 (5)
O1—Sn1'—C1'—C2'−46.9 (11)N5—N6—C42—S21.5 (8)
N1—Sn1'—C1'—C2'−129.6 (10)N8—N7—C42—N62.0 (8)
C5'—Sn1'—C1'—C2'66.6 (14)N8—N7—C42—S2−179.0 (4)
S1'—Sn1'—C1'—C2'159.1 (11)Sn2—S2—C42—N6−15.6 (6)
Sn1'—C1'—C2'—C3'−166.0 (9)Sn2—S2—C42—N7165.6 (4)
C1'—C2'—C3'—C4'−69.5 (18)N7—N8—C43—C45−176.8 (5)
O1—Sn1'—C5'—C6'−118.4 (14)N7—N8—C43—C442.0 (10)
N1—Sn1'—C5'—C6'−32.9 (17)N8—C43—C45—C46−176.2 (4)
C1'—Sn1'—C5'—C6'131.3 (13)C44—C43—C45—C465.0 (7)
S1'—Sn1'—C5'—C6'52.8 (16)N8—C43—C45—C506.6 (7)
Sn1'—C5'—C6'—C7'179.3 (12)C44—C43—C45—C50−172.3 (5)
C5'—C6'—C7'—C8'177.5 (17)C50—C45—C46—C470.0
Sn1—O1—C9—C10−127.2 (3)C43—C45—C46—C47−177.3 (5)
Sn1'—O1—C9—C10−126.2 (3)C45—C46—C47—C480.0
Sn1—O1—C9—C1451.6 (4)C46—C47—C48—C490.0
Sn1'—O1—C9—C1452.6 (4)C47—C48—C49—C500.0
O1—C9—C10—C11178.8 (4)C48—C49—C50—O4−179.5 (5)
C14—C9—C10—C110.0C48—C49—C50—C450.0
C9—C10—C11—C120.0C46—C45—C50—O4179.5 (6)
C10—C11—C12—C130.0C43—C45—C50—O4−3.3 (6)
C11—C12—C13—C140.0C46—C45—C50—C490.0
C12—C13—C14—C90.0C43—C45—C50—C49177.2 (5)
C12—C13—C14—C15178.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.862.243.054 (7)159
N7—H7···O3ii0.862.212.982 (7)150
O2—H2···N40.841.792.503 (8)141
O4—H4···N80.841.822.529 (8)141

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5030).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ren, Y.-P., Dai, R.-B., Wang, L.-F. & Wu, J.-G. (1999). Synth. Commun.29, 613–617.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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