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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2231-o2232

6,7,6′,7′-Tetra­phenyl-2,2′-bi[1,3-di­thia-5,8-di­aza­cyclo­penta­[b]naphthalenyl­­idene] chloro­form disolvate

aSchool of Chemistry, Univerisity of Hyderabad, Hyderabad 500 046, India
*Correspondence e-mail: skdsc@uohyd.ernet.in

(Received 12 May 2011; accepted 21 July 2011; online 2 August 2011)

The title compound, C42H24N4S4·2CHCl3, a symmetrical tetra­thia­fulvalene (TTF) derivative, was prepared by a tri­ethyl­phos­phite-mediated self-coupling reaction of 6,7-diphenyl-1,3-dithia-5,8-diaza­cyclo­penta­[b]napthalen-2-one. The asymmetric unit contains two TTF mol­ecules and four chloro­form solvent mol­ecules. Cl⋯Cl inter­actions [contact distances = 3.263 (1)–3.395 (2) Å] are present between the solvent mol­ecules, resulting in a tape along the bc plane. The crystal packing features weak C—H⋯Cl and C—H⋯N hydrogen bonds, resulting in the formation of a two-dimensional supramolecular network.

Related literature

For TTF chemistry, see: Bendikov et al. (2004[Bendikov, M., Wudl, F. & Perepichka, D. F. (2004). Chem. Rev. 104, 4891-4945.]). For conductors and super-conductors, see: Yamada et al. (2004[Yamada, J. & Sugimoto, T. (2004). In TTF Chemistry, Fundamentals and Application of Tetrathiafulvalene. Berlin: Springer.]); Otsubo & Takimiya (2004[Otsubo, T. & Takimiya, K. (2004). Bull. Chem. Soc. Jpn, 77, 43-58.]). For field effect transistors, see: Mas-Torrent et al. (2004[Mas-Torrent, M., Durkut, M., Hadley, P., Ribas, X. & Rovira, C. (2004). J. Am. Chem. Soc. 126, 984-985.]); Noda et al. (2005[Noda, B., Katsuhara, M., Aoyagi, I., Mori, T., Taguchi, T., Kambayashi, T., Ishikawa, K. & Takezoe, H. (2005). Chem. Lett. 34, 392-393.]); Naraso et al. (2005[Naraso, Nishida, J., Ando, S., Yamaguchi, J., Itaka, K., Koinuma, H., Tada, H., Tokito, S. & Yamashita, Y. (2005). J. Am. Chem. Soc. 127, 10142-10143.]). For the synthesis see: Bolligarla & Das (2011[Bolligarla, R. & Das, S. K. (2011). Tetrahedron Lett. 52, 2496-2500.]). For bond lengths in TTF derivatives, see: Bouguessa et al. (2003[Bouguessa, S., Gouasmia, A. K., Golhen, S., Ouahab, L. & Fabre, J. M. (2003). Tetrahedron Lett. 44, 9275-9278.]).

[Scheme 1]

Experimental

Crystal data
  • C42H24N4S4·2CHCl3

  • Mr = 951.63

  • Monoclinic, C c

  • a = 14.5359 (11) Å

  • b = 14.7543 (11) Å

  • c = 39.771 (3) Å

  • β = 97.616 (2)°

  • V = 8454.3 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.64 mm−1

  • T = 100 K

  • 0.48 × 0.36 × 0.14 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.748, Tmax = 0.915

  • 43023 measured reflections

  • 16629 independent reflections

  • 16092 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.109

  • S = 1.07

  • 16629 reflections

  • 1045 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.66 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯Cl2i 0.93 2.94 3.676 (4) 137
C85—H85⋯N2ii 0.98 2.31 3.233 (5) 156
C12—H12⋯N6iii 0.93 2.61 3.344 (4) 136
C86—H86⋯N3iv 0.98 2.29 3.223 (5) 158
C88—H88⋯N8iv 0.98 2.28 3.199 (5) 155
C87—H87⋯N5v 0.98 2.32 3.246 (5) 157
C60—H60⋯N1vi 0.93 2.63 3.392 (5) 139
C78—H78⋯N4vii 0.93 2.62 3.427 (4) 145
C42—H42⋯N7v 0.93 2.61 3.358 (4) 138
Symmetry codes: (i) x-1, y, z; (ii) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iii) x, y-1, z; (iv) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (v) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (vi) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (vii) x, y+1, z.

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Research interests on tetrathiafulvalene (TTF)–based compounds have remained dynamic in the field of materials science, particularly, in the context of molecular electronics and NLO materials, due to their unique π-donor properties. TTF and its derivatives have successfully been used as versatile building blocks for the formation of charge transfer salts giving rise to organic conductors and even super-conductors [see: Yamada et al. (2004); Otsubo et al. (2004)]. Furthermore, tetrathiafulvalene (TTF) derivatives are promising candidates for semiconductors leading to high performance FETs (Field Effect Transistors) because of their self-assembling properties. However, because of the strong electron-donating properties, the relevant thin films are generally labile to oxygen, resulting in poor FET performance. Naraso et al. have introduced fused aromatic rings or electron-deficient nitrogen heterocycles to the TTF skeleton to enhance the stability and obtained high hole mobilities in the thin films. In our previous letter [Bolligarla et al. (2011)], we have reported the synthesis and physical properties of acceptor-donor-acceptor (A—D—A) TTF (title compound). In solution state, emission behavior of this compound has also been described which is largely solvent dependent with huge Stokes shifts. In this contribution, we have reported the crystal structure and supramolecular feature of the title compound. The asymmetric unit contains two molecules of TTF triad and four molecules of chloroform (solvent) molecules as shown in Fig. 1(a). For clarity, one of the molecules present in the asymmetric unit is shown in Fig. 1(b). As shown in Fig. 1(b), the skeleton of the molecule is almost planar excluding the four peripheral phenyl groups. The r.m.s. deviation from a least-squares plane through the atoms of the core is 0.027 Å. The phenyl rings are deviated from the plane of skeleton of the molecule with angles in the range from 36.03° to 55.81°. The bond lengths in the TTF moiety are in the range of bond lengths, expected for neutral TTF derivatives. Interestingly, six Cl···Cl interactions are present between the solvent molecules resulting in the formation of a one dimensional chloroform tapes, and the Cl···Cl intermolecular contact distances are in the range from 3.263 (1) to 3. 395 (2) Å as shown in Fig. 2.

Related literature top

For TTF chemistry, see: Bendikov et al. (2004). For conductors and super-conductors, see: Yamada et al. (2004); Otsubo & Takimiya (2004). For field effect transistors, see: Mas-Torrent et al. (2004); Noda et al. (2005); Naraso et al. (2005). For the synthesis see: Bolligarla & Das (2011). For bond lengths in TTF derivatives, see: Bouguessa et al. (2003).

Experimental top

The title compound was synthesized according to literature procedure [Bolligarla et al. (2011)]. A solution of compound 6,7-diphenyl-1,3-dithia-5,8-diaza-cyclopenta[b]napthalen-2-one (125 mg, 0.336 mmol) in triethylphosphite (3 mL) was refluxed at 130–140 °C for 2 h under N2 atmosphere. After cooling to room temperature, MeOH (20 ml) was added and the resulting orange precipitate was filtered off (Yield: 70.0%). Single crystals of title compound, suitable for single-crystal X-ray analysis was obtained from chloroform in an NMR tube on slow evaporation over a period of two weeks.

Refinement top

All non-hydrogen atoms was refined anisotropically. The hydrogen atoms were included in the structure factor calculation by using a riding model.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. (a)Thermal ellipsoidal plot of the asymmetric unit of compound, the asymmetric unit contain two units of two TTF molecules and four chloroform solvent molecules. Hydrogen atoms are not shown for clarity (70% probability); (b)Thermal ellipsoidal plot of one of the molecules present in the asymmetric unit of the compound, Hydrogen atoms are not shown for clarity (70% probability).
[Figure 2] Fig. 2. The Cl···Cl interactions are between the chloroform solvent molecules to form a one dimensional tape.
[Figure 3] Fig. 3. The formation of the title compound.
[Figure 4] Fig. 4. Crystal packing diagram of the compound is described by C—H···N and C—H···Cl weak interactions resulting in two dimensional supramolecular network.
2-{6,7-dimethyl-2H-[1,3]dithiolo[4,5-g]quinoxalin-2-ylidene}- 6,7-dimethyl-2H-[1,3]dithiolo[4,5-g]quinoxaline top
Crystal data top
C42H24N4S4·2CHCl3F(000) = 3872
Mr = 951.63Dx = 1.495 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 8772 reflections
a = 14.5359 (11) Åθ = 2.3–26.2°
b = 14.7543 (11) ŵ = 0.64 mm1
c = 39.771 (3) ÅT = 100 K
β = 97.616 (2)°Block, brown
V = 8454.3 (11) Å30.48 × 0.36 × 0.14 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
16629 independent reflections
Radiation source: fine-focus sealed tube16092 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 26.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1817
Tmin = 0.748, Tmax = 0.915k = 1818
43023 measured reflectionsl = 4849
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0576P)2 + 12.7425P]
where P = (Fo2 + 2Fc2)/3
16629 reflections(Δ/σ)max = 0.001
1045 parametersΔρmax = 0.58 e Å3
2 restraintsΔρmin = 0.66 e Å3
Crystal data top
C42H24N4S4·2CHCl3V = 8454.3 (11) Å3
Mr = 951.63Z = 8
Monoclinic, CcMo Kα radiation
a = 14.5359 (11) ŵ = 0.64 mm1
b = 14.7543 (11) ÅT = 100 K
c = 39.771 (3) Å0.48 × 0.36 × 0.14 mm
β = 97.616 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
16629 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
16092 reflections with I > 2σ(I)
Tmin = 0.748, Tmax = 0.915Rint = 0.029
43023 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0422 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0576P)2 + 12.7425P]
where P = (Fo2 + 2Fc2)/3
16629 reflectionsΔρmax = 0.58 e Å3
1045 parametersΔρmin = 0.66 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Absolute structure of the title compound could not be determined unambigously due to the lack of enough contribution towards anomalous dispersion by the non hydrogen atoms present and therefore, the Flack parameter is not reported.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S50.12002 (6)0.93290 (6)0.57016 (2)0.02468 (18)
S40.58994 (6)0.14264 (6)0.51422 (2)0.02435 (18)
S80.35756 (6)0.86813 (6)0.51766 (2)0.02512 (18)
S10.37317 (6)0.14711 (6)0.58085 (2)0.02433 (18)
S70.22618 (6)1.02323 (6)0.51246 (2)0.02470 (18)
S30.44035 (6)0.27438 (6)0.52303 (2)0.02481 (18)
S60.25227 (6)0.77850 (6)0.57503 (2)0.02452 (18)
S20.52343 (6)0.01627 (6)0.57179 (2)0.02431 (18)
C680.4590 (2)1.0229 (2)0.44690 (8)0.0207 (7)
N70.39830 (19)1.16091 (19)0.42016 (7)0.0210 (6)
N30.5599 (2)0.4788 (2)0.43348 (7)0.0232 (6)
C170.2316 (2)0.1369 (2)0.72103 (8)0.0195 (7)
C310.7318 (2)0.4258 (2)0.37375 (8)0.0209 (7)
N60.08049 (19)0.63969 (19)0.66733 (7)0.0208 (6)
C260.6392 (2)0.3373 (2)0.44750 (8)0.0207 (7)
N20.40713 (19)0.18868 (19)0.66189 (7)0.0207 (6)
C70.3249 (2)0.0484 (2)0.64744 (8)0.0203 (7)
N40.69477 (19)0.34997 (19)0.42295 (7)0.0205 (6)
C800.4410 (2)1.3117 (2)0.37982 (8)0.0231 (7)
H800.43651.32810.40210.028*
N50.0499 (2)0.78039 (19)0.66059 (7)0.0201 (6)
C490.0203 (2)0.7780 (2)0.64082 (8)0.0208 (7)
C270.5694 (2)0.4015 (2)0.45210 (8)0.0208 (7)
C30.3766 (2)0.0475 (2)0.60497 (8)0.0204 (7)
C720.5312 (2)1.0836 (2)0.40408 (8)0.0205 (7)
C530.0259 (2)0.5814 (2)0.71666 (8)0.0198 (7)
N80.52848 (19)1.0185 (2)0.42723 (7)0.0217 (6)
C700.3237 (2)1.0982 (2)0.46466 (8)0.0220 (7)
H700.28301.14710.46330.026*
C790.4564 (2)1.2221 (2)0.37206 (8)0.0206 (7)
N10.27045 (19)0.06132 (19)0.67222 (7)0.0217 (6)
C480.0841 (2)0.7047 (2)0.64326 (8)0.0213 (7)
C50.4564 (2)0.0944 (2)0.61861 (8)0.0214 (7)
H50.50130.13660.61470.026*
C230.5161 (2)0.3050 (2)0.49429 (8)0.0215 (7)
C60.3965 (2)0.1118 (2)0.64298 (8)0.0195 (7)
C520.0166 (2)0.6463 (2)0.68797 (8)0.0195 (7)
C460.1639 (2)0.7729 (2)0.60089 (8)0.0200 (7)
C710.4624 (2)1.1536 (2)0.39973 (8)0.0206 (7)
C630.2366 (3)0.8073 (3)0.73290 (9)0.0287 (8)
H630.25550.86290.74060.034*
C370.6026 (2)0.5772 (2)0.39069 (8)0.0211 (7)
C730.6101 (2)1.0780 (2)0.38364 (8)0.0232 (7)
C430.2165 (2)0.8821 (2)0.55573 (8)0.0225 (7)
C470.1552 (2)0.7027 (2)0.62264 (8)0.0220 (7)
H470.19620.65400.62380.026*
C160.4548 (2)0.3216 (2)0.71374 (8)0.0205 (7)
H160.50610.28930.70860.025*
C40.4483 (2)0.0150 (2)0.60068 (8)0.0194 (6)
C750.7122 (3)0.9879 (3)0.35420 (10)0.0292 (8)
H750.73120.93150.34730.035*
C640.1626 (2)0.8035 (2)0.71444 (9)0.0244 (7)
H640.13320.85660.70920.029*
C80.3153 (2)0.0312 (2)0.62766 (8)0.0216 (7)
H80.26790.07220.63000.026*
C590.1318 (2)0.7194 (2)0.70355 (8)0.0198 (7)
C220.1364 (2)0.1222 (2)0.71611 (9)0.0228 (7)
H220.10630.10970.69450.027*
C360.8284 (3)0.4120 (2)0.37773 (9)0.0256 (7)
H360.86050.40170.39920.031*
C240.5876 (2)0.2414 (2)0.49009 (8)0.0205 (7)
C650.3148 (2)1.0287 (2)0.48684 (8)0.0207 (7)
C450.1000 (2)0.8464 (2)0.59820 (8)0.0215 (7)
C180.2760 (3)0.1517 (3)0.75389 (9)0.0289 (8)
H180.33990.16020.75750.035*
C690.3949 (2)1.0949 (2)0.44409 (9)0.0216 (7)
C110.3653 (2)0.2869 (2)0.70489 (8)0.0211 (7)
C250.6484 (2)0.2580 (2)0.46729 (8)0.0220 (7)
H250.69570.21690.46490.026*
C670.4498 (2)0.9523 (2)0.47032 (8)0.0225 (7)
H670.49230.90490.47270.027*
C280.5076 (2)0.3840 (2)0.47621 (8)0.0219 (7)
H280.46180.42580.47960.026*
C100.3537 (2)0.2001 (2)0.68596 (8)0.0210 (7)
C20.4958 (2)0.1718 (2)0.53564 (8)0.0217 (7)
C740.6393 (2)0.9941 (2)0.37293 (9)0.0251 (7)
H740.60920.94170.37850.030*
C510.0528 (2)0.7167 (2)0.68359 (8)0.0208 (7)
C10.4669 (2)0.1187 (2)0.55954 (8)0.0225 (7)
C380.5142 (2)0.6136 (2)0.38140 (9)0.0252 (7)
H380.46220.58310.38680.030*
C300.6805 (2)0.4221 (2)0.40339 (8)0.0195 (7)
C780.6585 (2)1.1555 (2)0.37596 (9)0.0242 (7)
H780.64141.21170.38370.029*
C610.2542 (3)0.6465 (3)0.72855 (9)0.0273 (8)
H610.28620.59410.73290.033*
C290.6135 (2)0.4903 (2)0.40974 (8)0.0199 (7)
C600.1785 (2)0.6410 (2)0.71077 (8)0.0227 (7)
H600.15910.58490.70370.027*
C410.6691 (3)0.7090 (3)0.36691 (9)0.0266 (8)
H410.72100.74170.36270.032*
C540.0349 (2)0.4884 (2)0.71084 (9)0.0246 (7)
H540.03180.46660.68880.030*
C500.0281 (2)0.8484 (2)0.61736 (8)0.0214 (7)
H500.01480.89550.61490.026*
C660.3785 (2)0.9539 (2)0.48946 (8)0.0214 (7)
C90.2856 (2)0.1324 (2)0.69186 (8)0.0213 (7)
C400.5808 (3)0.7428 (2)0.35680 (9)0.0264 (7)
H400.57290.79740.34510.032*
C210.0860 (3)0.1262 (2)0.74348 (10)0.0271 (8)
H210.02200.11790.74000.032*
C580.0324 (3)0.6119 (2)0.75016 (9)0.0269 (7)
H580.02580.67330.75450.032*
C330.7330 (3)0.4383 (3)0.31369 (10)0.0328 (8)
H330.70080.44600.29210.039*
C140.3904 (3)0.4529 (2)0.73799 (9)0.0263 (7)
H140.39860.50830.74910.032*
C440.2612 (2)0.9198 (2)0.53193 (8)0.0216 (7)
C810.4321 (3)1.3774 (3)0.35454 (10)0.0320 (8)
H810.42111.43750.35990.038*
C770.7313 (3)1.1497 (3)0.35712 (10)0.0308 (8)
H770.76291.20170.35210.037*
C420.6796 (2)0.6263 (2)0.38336 (8)0.0226 (7)
H420.73880.60300.38960.027*
C130.3022 (3)0.4186 (2)0.72916 (9)0.0265 (7)
H130.25100.45140.73410.032*
C320.6861 (2)0.4391 (3)0.34140 (9)0.0274 (8)
H320.62230.44890.33840.033*
C550.0485 (2)0.4289 (2)0.73784 (10)0.0284 (8)
H550.05240.36710.73370.034*
C390.5040 (3)0.6944 (2)0.36430 (9)0.0280 (8)
H390.44470.71710.35760.034*
C760.7571 (2)1.0655 (3)0.34570 (9)0.0302 (8)
H760.80481.06140.33230.036*
C350.8754 (3)0.4136 (3)0.34986 (10)0.0315 (8)
H350.93950.40630.35270.038*
C150.4667 (2)0.4050 (2)0.73035 (9)0.0250 (7)
H150.52610.42830.73630.030*
C620.2825 (3)0.7294 (3)0.73994 (9)0.0292 (8)
H620.33250.73240.75230.035*
C340.8282 (3)0.4260 (3)0.31783 (10)0.0322 (8)
H340.86020.42610.29910.039*
C560.0565 (2)0.4594 (3)0.77062 (10)0.0296 (8)
H560.06710.41880.78860.036*
C190.2261 (3)0.1538 (3)0.78084 (9)0.0325 (8)
H190.25670.16290.80260.039*
C570.0484 (3)0.5518 (3)0.77677 (10)0.0303 (8)
H570.05380.57300.79900.036*
C830.4533 (3)1.2638 (3)0.31343 (10)0.0340 (9)
H830.45721.24750.29110.041*
C840.4615 (2)1.1974 (3)0.33861 (9)0.0268 (7)
H840.47031.13710.33310.032*
C820.4396 (3)1.3532 (3)0.32132 (10)0.0350 (9)
H820.43541.39710.30440.042*
C200.1307 (3)0.1424 (3)0.77592 (9)0.0295 (8)
H200.09700.14570.79420.035*
C120.2895 (2)0.3356 (2)0.71289 (9)0.0244 (7)
H120.22990.31250.70730.029*
Cl80.19602 (6)0.45268 (6)0.64885 (2)0.03064 (19)
Cl50.10844 (6)0.22596 (6)0.44357 (2)0.0317 (2)
Cl120.27482 (6)0.34015 (6)0.44034 (2)0.0313 (2)
Cl30.99363 (8)0.14803 (9)0.58894 (3)0.0480 (3)
Cl40.02752 (9)0.13926 (9)0.50589 (3)0.0495 (3)
Cl100.22187 (9)0.41714 (9)0.50180 (3)0.0539 (3)
Cl110.28527 (8)0.53372 (7)0.45119 (4)0.0497 (3)
Cl90.25430 (9)0.38265 (9)0.58694 (3)0.0515 (3)
Cl70.18825 (8)0.26046 (7)0.63526 (4)0.0513 (3)
C870.2487 (3)0.3614 (3)0.63006 (10)0.0308 (8)
H870.31220.35470.64160.037*
C880.2241 (3)0.4340 (3)0.45824 (10)0.0310 (8)
H880.16010.44040.44720.037*
Cl10.88234 (7)0.06387 (8)0.63569 (3)0.0472 (3)
Cl60.09042 (8)0.22708 (8)0.46238 (4)0.0553 (3)
C860.0125 (3)0.1644 (3)0.46373 (10)0.0332 (8)
H860.00780.10740.45150.040*
C850.9839 (3)0.1270 (3)0.63160 (10)0.0323 (8)
H850.98020.18520.64320.039*
Cl21.08202 (6)0.06723 (6)0.65138 (2)0.03064 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S50.0254 (4)0.0253 (4)0.0246 (4)0.0057 (3)0.0081 (3)0.0018 (3)
S40.0264 (4)0.0197 (4)0.0264 (4)0.0062 (3)0.0018 (3)0.0033 (3)
S80.0252 (4)0.0237 (4)0.0281 (4)0.0055 (3)0.0095 (3)0.0000 (3)
S10.0260 (4)0.0205 (4)0.0261 (4)0.0069 (3)0.0017 (3)0.0028 (3)
S70.0236 (4)0.0260 (4)0.0257 (4)0.0068 (3)0.0075 (3)0.0012 (3)
S30.0269 (4)0.0226 (4)0.0253 (4)0.0067 (3)0.0050 (3)0.0049 (3)
S60.0220 (4)0.0259 (4)0.0268 (4)0.0045 (3)0.0075 (3)0.0016 (3)
S20.0260 (4)0.0200 (4)0.0275 (4)0.0060 (3)0.0056 (3)0.0044 (3)
C680.0197 (16)0.0226 (17)0.0187 (15)0.0020 (13)0.0020 (12)0.0048 (12)
N70.0194 (14)0.0232 (15)0.0193 (14)0.0027 (11)0.0013 (11)0.0024 (11)
N30.0265 (15)0.0206 (14)0.0216 (14)0.0043 (12)0.0000 (11)0.0013 (11)
C170.0227 (16)0.0140 (15)0.0219 (16)0.0014 (12)0.0030 (13)0.0022 (12)
C310.0218 (16)0.0165 (16)0.0242 (17)0.0049 (13)0.0019 (13)0.0044 (13)
N60.0208 (14)0.0187 (14)0.0221 (14)0.0035 (11)0.0000 (11)0.0028 (11)
C260.0206 (16)0.0203 (16)0.0206 (16)0.0004 (13)0.0007 (12)0.0064 (13)
N20.0204 (14)0.0163 (13)0.0245 (14)0.0046 (11)0.0006 (11)0.0006 (11)
C70.0205 (16)0.0200 (16)0.0194 (15)0.0028 (13)0.0013 (12)0.0038 (13)
N40.0201 (14)0.0217 (14)0.0187 (13)0.0016 (11)0.0013 (11)0.0028 (11)
C800.0164 (15)0.0318 (19)0.0207 (16)0.0022 (14)0.0012 (12)0.0008 (14)
N50.0209 (14)0.0196 (14)0.0199 (13)0.0025 (11)0.0025 (11)0.0013 (11)
C490.0174 (15)0.0261 (18)0.0185 (15)0.0052 (13)0.0005 (12)0.0032 (13)
C270.0214 (16)0.0194 (16)0.0203 (16)0.0037 (13)0.0020 (13)0.0017 (13)
C30.0254 (17)0.0160 (16)0.0179 (15)0.0038 (13)0.0043 (13)0.0012 (12)
C720.0187 (16)0.0251 (17)0.0177 (15)0.0004 (13)0.0020 (12)0.0073 (13)
C530.0138 (15)0.0217 (17)0.0234 (16)0.0037 (12)0.0010 (12)0.0004 (13)
N80.0148 (13)0.0258 (15)0.0243 (14)0.0029 (11)0.0020 (11)0.0054 (12)
C700.0238 (17)0.0216 (17)0.0203 (16)0.0053 (13)0.0013 (13)0.0045 (13)
C790.0131 (15)0.0232 (17)0.0248 (16)0.0001 (13)0.0001 (12)0.0011 (13)
N10.0186 (14)0.0193 (14)0.0265 (15)0.0030 (11)0.0009 (11)0.0036 (11)
C480.0193 (16)0.0243 (17)0.0198 (16)0.0011 (13)0.0006 (12)0.0042 (13)
C50.0198 (16)0.0194 (16)0.0240 (17)0.0047 (13)0.0005 (13)0.0019 (13)
C230.0237 (16)0.0204 (17)0.0193 (16)0.0014 (13)0.0012 (13)0.0010 (12)
C60.0223 (16)0.0154 (15)0.0195 (16)0.0003 (13)0.0023 (13)0.0047 (12)
C520.0181 (15)0.0221 (17)0.0180 (15)0.0005 (13)0.0016 (12)0.0041 (12)
C460.0144 (15)0.0285 (18)0.0167 (15)0.0029 (13)0.0012 (12)0.0054 (13)
C710.0162 (15)0.0222 (17)0.0220 (16)0.0005 (13)0.0030 (12)0.0049 (13)
C630.0259 (19)0.028 (2)0.032 (2)0.0086 (15)0.0062 (15)0.0042 (15)
C370.0234 (16)0.0194 (16)0.0204 (16)0.0024 (13)0.0028 (13)0.0043 (13)
C730.0184 (16)0.0300 (19)0.0202 (16)0.0019 (14)0.0007 (13)0.0051 (13)
C430.0179 (16)0.0276 (18)0.0221 (17)0.0054 (14)0.0030 (13)0.0039 (14)
C470.0214 (16)0.0223 (17)0.0215 (16)0.0090 (13)0.0004 (13)0.0017 (13)
C160.0220 (16)0.0161 (16)0.0237 (17)0.0016 (13)0.0040 (13)0.0014 (12)
C40.0204 (16)0.0196 (16)0.0175 (15)0.0001 (13)0.0005 (12)0.0024 (12)
C750.0248 (18)0.029 (2)0.0340 (19)0.0036 (15)0.0058 (15)0.0063 (15)
C640.0197 (16)0.0250 (18)0.0280 (18)0.0034 (14)0.0018 (13)0.0016 (14)
C80.0206 (16)0.0193 (16)0.0246 (16)0.0081 (13)0.0016 (13)0.0018 (13)
C590.0158 (15)0.0212 (16)0.0213 (16)0.0062 (13)0.0014 (12)0.0011 (13)
C220.0214 (17)0.0158 (16)0.0301 (18)0.0043 (13)0.0005 (14)0.0017 (13)
C360.0264 (18)0.0192 (17)0.0301 (18)0.0053 (14)0.0002 (14)0.0031 (14)
C240.0226 (16)0.0154 (16)0.0222 (16)0.0004 (13)0.0010 (13)0.0009 (12)
C650.0189 (16)0.0251 (18)0.0181 (16)0.0003 (13)0.0015 (12)0.0048 (13)
C450.0228 (17)0.0233 (17)0.0176 (15)0.0014 (13)0.0001 (13)0.0022 (13)
C180.0210 (17)0.038 (2)0.0279 (18)0.0074 (15)0.0023 (14)0.0026 (16)
C690.0194 (16)0.0218 (17)0.0228 (16)0.0044 (13)0.0003 (12)0.0050 (13)
C110.0255 (17)0.0207 (17)0.0163 (15)0.0032 (13)0.0005 (13)0.0028 (12)
C250.0238 (17)0.0187 (16)0.0218 (17)0.0055 (13)0.0028 (13)0.0004 (13)
C670.0196 (16)0.0234 (17)0.0239 (17)0.0051 (13)0.0012 (13)0.0030 (13)
C280.0213 (16)0.0212 (17)0.0229 (17)0.0064 (14)0.0017 (13)0.0021 (13)
C100.0201 (16)0.0185 (16)0.0229 (17)0.0039 (13)0.0023 (13)0.0061 (13)
C20.0243 (16)0.0174 (16)0.0225 (16)0.0077 (13)0.0009 (13)0.0006 (12)
C740.0211 (17)0.0235 (18)0.0308 (18)0.0012 (14)0.0036 (14)0.0028 (14)
C510.0175 (16)0.0248 (17)0.0192 (16)0.0018 (13)0.0017 (12)0.0045 (13)
C10.0248 (17)0.0195 (17)0.0219 (16)0.0047 (14)0.0015 (13)0.0012 (13)
C380.0252 (18)0.0240 (18)0.0274 (18)0.0007 (14)0.0066 (14)0.0003 (14)
C300.0178 (15)0.0174 (16)0.0223 (16)0.0023 (12)0.0013 (12)0.0046 (12)
C780.0210 (17)0.0212 (18)0.0297 (18)0.0029 (14)0.0007 (14)0.0052 (14)
C610.0250 (18)0.0298 (19)0.0263 (18)0.0002 (15)0.0008 (14)0.0062 (14)
C290.0200 (16)0.0220 (17)0.0169 (15)0.0012 (13)0.0007 (12)0.0025 (13)
C600.0209 (16)0.0274 (18)0.0187 (16)0.0064 (14)0.0018 (13)0.0006 (13)
C410.0289 (19)0.0271 (18)0.0240 (17)0.0015 (15)0.0045 (14)0.0040 (14)
C540.0183 (16)0.0246 (18)0.0311 (18)0.0041 (14)0.0036 (14)0.0048 (14)
C500.0205 (16)0.0258 (18)0.0175 (15)0.0056 (13)0.0007 (12)0.0020 (13)
C660.0189 (16)0.0238 (17)0.0202 (16)0.0025 (13)0.0027 (12)0.0026 (13)
C90.0190 (16)0.0220 (17)0.0216 (16)0.0013 (13)0.0015 (13)0.0018 (13)
C400.036 (2)0.0211 (17)0.0224 (17)0.0044 (15)0.0046 (15)0.0032 (13)
C210.0225 (17)0.0210 (17)0.038 (2)0.0045 (14)0.0061 (15)0.0005 (15)
C580.0288 (18)0.0223 (18)0.0285 (18)0.0059 (14)0.0000 (14)0.0040 (14)
C330.0308 (19)0.044 (2)0.0239 (18)0.0059 (17)0.0039 (15)0.0037 (16)
C140.038 (2)0.0162 (16)0.0250 (18)0.0048 (14)0.0034 (15)0.0006 (13)
C440.0205 (16)0.0234 (17)0.0208 (16)0.0067 (13)0.0022 (13)0.0056 (13)
C810.0241 (18)0.0251 (19)0.045 (2)0.0022 (15)0.0006 (16)0.0037 (16)
C770.0231 (18)0.030 (2)0.040 (2)0.0013 (15)0.0053 (15)0.0027 (16)
C420.0238 (17)0.0247 (18)0.0188 (16)0.0035 (14)0.0018 (13)0.0063 (13)
C130.0262 (18)0.0212 (17)0.0326 (19)0.0046 (14)0.0064 (15)0.0034 (14)
C320.0212 (17)0.032 (2)0.0290 (18)0.0043 (14)0.0017 (14)0.0069 (15)
C550.0209 (17)0.0177 (17)0.046 (2)0.0041 (13)0.0032 (15)0.0028 (15)
C390.0285 (18)0.0241 (18)0.0306 (19)0.0090 (15)0.0012 (15)0.0013 (14)
C760.0187 (16)0.044 (2)0.0300 (19)0.0001 (15)0.0093 (14)0.0029 (16)
C350.0211 (18)0.030 (2)0.045 (2)0.0027 (15)0.0098 (16)0.0022 (16)
C150.0247 (17)0.0222 (17)0.0271 (18)0.0094 (14)0.0003 (14)0.0001 (14)
C620.0242 (18)0.038 (2)0.0263 (18)0.0062 (16)0.0087 (14)0.0010 (15)
C340.037 (2)0.034 (2)0.0293 (19)0.0047 (16)0.0155 (16)0.0006 (15)
C560.0245 (18)0.0292 (19)0.036 (2)0.0063 (15)0.0068 (15)0.0086 (15)
C190.034 (2)0.044 (2)0.0191 (17)0.0087 (17)0.0033 (14)0.0009 (15)
C570.035 (2)0.0302 (19)0.0262 (18)0.0031 (16)0.0038 (15)0.0011 (15)
C830.032 (2)0.046 (2)0.0235 (18)0.0090 (17)0.0003 (15)0.0016 (16)
C840.0222 (16)0.0299 (19)0.0282 (18)0.0025 (14)0.0025 (14)0.0058 (15)
C820.028 (2)0.042 (2)0.033 (2)0.0046 (17)0.0042 (15)0.0110 (17)
C200.0295 (19)0.033 (2)0.0285 (19)0.0038 (16)0.0115 (15)0.0007 (15)
C120.0228 (17)0.0215 (17)0.0278 (18)0.0019 (14)0.0006 (14)0.0040 (14)
Cl80.0284 (4)0.0303 (5)0.0336 (5)0.0075 (4)0.0059 (4)0.0005 (4)
Cl50.0323 (5)0.0290 (5)0.0348 (5)0.0064 (4)0.0081 (4)0.0012 (4)
Cl120.0303 (5)0.0274 (4)0.0369 (5)0.0039 (4)0.0065 (4)0.0034 (4)
Cl30.0526 (6)0.0589 (7)0.0309 (5)0.0177 (5)0.0004 (5)0.0042 (5)
Cl40.0617 (7)0.0542 (7)0.0312 (5)0.0169 (6)0.0012 (5)0.0016 (5)
Cl100.0671 (8)0.0633 (8)0.0297 (5)0.0260 (6)0.0004 (5)0.0062 (5)
Cl110.0380 (6)0.0282 (5)0.0789 (8)0.0028 (4)0.0071 (5)0.0001 (5)
Cl90.0672 (8)0.0572 (7)0.0292 (5)0.0254 (6)0.0032 (5)0.0019 (5)
Cl70.0368 (6)0.0286 (5)0.0854 (9)0.0058 (4)0.0036 (6)0.0016 (5)
C870.032 (2)0.0295 (19)0.0300 (19)0.0103 (16)0.0002 (15)0.0013 (15)
C880.0272 (19)0.0308 (19)0.033 (2)0.0077 (16)0.0043 (15)0.0030 (16)
Cl10.0266 (5)0.0371 (6)0.0780 (8)0.0024 (4)0.0067 (5)0.0134 (5)
Cl60.0304 (5)0.0353 (6)0.1000 (10)0.0036 (4)0.0084 (6)0.0069 (6)
C860.0301 (19)0.031 (2)0.039 (2)0.0061 (16)0.0042 (16)0.0035 (16)
C850.030 (2)0.031 (2)0.036 (2)0.0109 (16)0.0018 (16)0.0056 (16)
Cl20.0274 (4)0.0296 (5)0.0350 (5)0.0050 (4)0.0044 (4)0.0001 (4)
Geometric parameters (Å, º) top
S5—C451.745 (4)C59—C511.480 (5)
S5—C431.753 (3)C22—C211.392 (5)
S4—C241.743 (3)C22—H220.9300
S4—C21.759 (4)C36—C351.377 (5)
S8—C661.744 (4)C36—H360.9300
S8—C441.754 (3)C24—C251.370 (5)
S1—C11.748 (4)C65—C661.435 (5)
S1—C31.752 (3)C45—C501.373 (5)
S7—C651.748 (3)C18—C191.372 (5)
S7—C441.755 (4)C18—H180.9300
S3—C231.748 (3)C11—C121.388 (5)
S3—C21.756 (3)C11—C101.484 (5)
S6—C461.751 (3)C25—H250.9300
S6—C431.758 (4)C67—C661.365 (5)
S2—C41.749 (3)C67—H670.9300
S2—C11.758 (3)C28—H280.9300
C68—N81.358 (4)C10—C91.447 (5)
C68—C691.409 (5)C2—C11.341 (5)
C68—C671.415 (5)C74—H740.9300
N7—C711.319 (4)C38—C391.370 (5)
N7—C691.367 (4)C38—H380.9300
N3—C291.312 (4)C30—C291.447 (5)
N3—C271.358 (4)C78—C771.377 (5)
C17—C221.389 (5)C78—H780.9300
C17—C181.396 (5)C61—C601.386 (5)
C17—C91.486 (5)C61—C621.386 (5)
C31—C321.382 (5)C61—H610.9300
C31—C361.406 (5)C60—H600.9300
C31—C301.477 (5)C41—C421.383 (5)
N6—C521.322 (4)C41—C401.387 (5)
N6—C481.361 (4)C41—H410.9300
C26—N41.360 (4)C54—C551.380 (5)
C26—C251.407 (5)C54—H540.9300
C26—C271.417 (5)C50—H500.9300
N2—C101.321 (5)C40—C391.391 (5)
N2—C61.358 (4)C40—H400.9300
C7—N11.356 (4)C21—C201.387 (5)
C7—C81.410 (5)C21—H210.9300
C7—C61.428 (5)C58—C571.377 (5)
N4—C301.318 (4)C58—H580.9300
C80—C791.383 (5)C33—C321.371 (5)
C80—C811.391 (5)C33—C341.384 (6)
C80—H800.9300C33—H330.9300
N5—C511.316 (4)C14—C131.380 (5)
N5—C491.368 (4)C14—C151.382 (5)
C49—C501.412 (5)C14—H140.9300
C49—C481.419 (5)C81—C821.387 (6)
C27—C281.422 (5)C81—H810.9300
C3—C81.371 (5)C77—C761.392 (6)
C3—C41.419 (5)C77—H770.9300
C72—N81.335 (5)C42—H420.9300
C72—C711.433 (5)C13—C121.386 (5)
C72—C731.493 (5)C13—H130.9300
C53—C581.397 (5)C32—H320.9300
C53—C541.402 (5)C55—C561.370 (6)
C53—C521.482 (5)C55—H550.9300
C70—C651.370 (5)C39—H390.9300
C70—C691.402 (5)C76—H760.9300
C70—H700.9300C35—C341.377 (6)
C79—C841.391 (5)C35—H350.9300
C79—C711.488 (5)C15—H150.9300
N1—C91.309 (4)C62—H620.9300
C48—C471.403 (5)C34—H340.9300
C5—C41.367 (5)C56—C571.392 (5)
C5—C61.411 (5)C56—H560.9300
C5—H50.9300C19—C201.384 (6)
C23—C281.367 (5)C19—H190.9300
C23—C241.426 (5)C57—H570.9300
C52—C511.443 (5)C83—C821.376 (6)
C46—C471.365 (5)C83—C841.395 (5)
C46—C451.422 (5)C83—H830.9300
C63—C621.376 (6)C84—H840.9300
C63—C641.381 (5)C82—H820.9300
C63—H630.9300C20—H200.9300
C37—C421.396 (5)C12—H120.9300
C37—C381.397 (5)Cl8—C871.764 (4)
C37—C291.486 (5)Cl5—C861.765 (4)
C73—C741.393 (5)Cl12—C881.762 (4)
C73—C781.397 (5)Cl3—C851.749 (4)
C43—C441.338 (5)Cl4—C861.759 (4)
C47—H470.9300Cl10—C881.755 (4)
C16—C151.396 (5)Cl11—C881.760 (4)
C16—C111.398 (5)Cl9—C871.756 (4)
C16—H160.9300Cl7—C871.755 (4)
C75—C741.377 (5)C87—H870.9800
C75—C761.381 (6)C88—H880.9800
C75—H750.9300Cl1—C851.771 (4)
C64—C591.407 (5)Cl6—C861.765 (4)
C64—H640.9300C86—H860.9800
C8—H80.9300C85—Cl21.770 (4)
C59—C601.391 (5)C85—H850.9800
C45—S5—C4396.02 (17)C1—C2—S4122.5 (2)
C24—S4—C295.88 (16)S3—C2—S4115.43 (19)
C66—S8—C4496.17 (16)C75—C74—C73120.8 (3)
C1—S1—C395.57 (16)C75—C74—H74119.6
C65—S7—C4495.98 (16)C73—C74—H74119.6
C23—S3—C296.00 (16)N5—C51—C52120.7 (3)
C46—S6—C4395.76 (16)N5—C51—C59117.0 (3)
C4—S2—C195.70 (16)C52—C51—C59122.3 (3)
N8—C68—C69121.7 (3)C2—C1—S1122.7 (2)
N8—C68—C67119.1 (3)C2—C1—S2121.3 (2)
C69—C68—C67119.2 (3)S1—C1—S2115.9 (2)
C71—N7—C69117.7 (3)C39—C38—C37120.1 (3)
C29—N3—C27118.3 (3)C39—C38—H38119.9
C22—C17—C18119.0 (3)C37—C38—H38119.9
C22—C17—C9120.2 (3)N4—C30—C29121.0 (3)
C18—C17—C9120.8 (3)N4—C30—C31116.4 (3)
C32—C31—C36118.4 (3)C29—C30—C31122.4 (3)
C32—C31—C30121.1 (3)C77—C78—C73120.9 (3)
C36—C31—C30120.4 (3)C77—C78—H78119.6
C52—N6—C48118.7 (3)C73—C78—H78119.6
N4—C26—C25119.6 (3)C60—C61—C62120.6 (3)
N4—C26—C27120.3 (3)C60—C61—H61119.7
C25—C26—C27120.0 (3)C62—C61—H61119.7
C10—N2—C6118.2 (3)N3—C29—C30120.9 (3)
N1—C7—C8119.9 (3)N3—C29—C37116.4 (3)
N1—C7—C6120.2 (3)C30—C29—C37122.7 (3)
C8—C7—C6119.8 (3)C61—C60—C59119.9 (3)
C30—N4—C26118.2 (3)C61—C60—H60120.0
C79—C80—C81120.5 (3)C59—C60—H60120.0
C79—C80—H80119.7C42—C41—C40119.6 (3)
C81—C80—H80119.7C42—C41—H41120.2
C51—N5—C49118.5 (3)C40—C41—H41120.2
N5—C49—C50119.5 (3)C55—C54—C53120.1 (3)
N5—C49—C48120.7 (3)C55—C54—H54120.0
C50—C49—C48119.8 (3)C53—C54—H54120.0
N3—C27—C26121.0 (3)C45—C50—C49119.0 (3)
N3—C27—C28119.5 (3)C45—C50—H50120.5
C26—C27—C28119.5 (3)C49—C50—H50120.5
C8—C3—C4121.1 (3)C67—C66—C65120.2 (3)
C8—C3—S1122.3 (3)C67—C66—S8123.8 (3)
C4—C3—S1116.6 (3)C65—C66—S8116.0 (2)
N8—C72—C71121.2 (3)N1—C9—C10121.4 (3)
N8—C72—C73115.5 (3)N1—C9—C17115.9 (3)
C71—C72—C73123.3 (3)C10—C9—C17122.6 (3)
C58—C53—C54118.5 (3)C41—C40—C39119.4 (3)
C58—C53—C52120.9 (3)C41—C40—H40120.3
C54—C53—C52120.5 (3)C39—C40—H40120.3
C72—N8—C68117.1 (3)C20—C21—C22120.3 (3)
C65—C70—C69119.3 (3)C20—C21—H21119.8
C65—C70—H70120.4C22—C21—H21119.8
C69—C70—H70120.4C57—C58—C53120.6 (3)
C80—C79—C84119.6 (3)C57—C58—H58119.7
C80—C79—C71118.7 (3)C53—C58—H58119.7
C84—C79—C71121.6 (3)C32—C33—C34120.1 (4)
C9—N1—C7118.5 (3)C32—C33—H33119.9
N6—C48—C47119.8 (3)C34—C33—H33119.9
N6—C48—C49120.0 (3)C13—C14—C15120.1 (3)
C47—C48—C49120.1 (3)C13—C14—H14119.9
C4—C5—C6119.7 (3)C15—C14—H14119.9
C4—C5—H5120.1C43—C44—S8122.1 (2)
C6—C5—H5120.1C43—C44—S7122.3 (2)
C28—C23—C24121.1 (3)S8—C44—S7115.6 (2)
C28—C23—S3122.9 (3)C82—C81—C80119.8 (4)
C24—C23—S3116.0 (3)C82—C81—H81120.1
N2—C6—C5119.8 (3)C80—C81—H81120.1
N2—C6—C7120.7 (3)C78—C77—C76119.6 (3)
C5—C6—C7119.5 (3)C78—C77—H77120.2
N6—C52—C51121.0 (3)C76—C77—H77120.2
N6—C52—C53115.5 (3)C41—C42—C37121.0 (3)
C51—C52—C53123.3 (3)C41—C42—H42119.5
C47—C46—C45120.8 (3)C37—C42—H42119.5
C47—C46—S6123.0 (3)C14—C13—C12120.3 (3)
C45—C46—S6116.3 (3)C14—C13—H13119.9
N7—C71—C72121.6 (3)C12—C13—H13119.9
N7—C71—C79115.0 (3)C33—C32—C31121.2 (3)
C72—C71—C79123.4 (3)C33—C32—H32119.4
C62—C63—C64120.5 (3)C31—C32—H32119.4
C62—C63—H63119.8C56—C55—C54121.1 (3)
C64—C63—H63119.8C56—C55—H55119.4
C42—C37—C38118.7 (3)C54—C55—H55119.4
C42—C37—C29121.3 (3)C38—C39—C40121.1 (3)
C38—C37—C29120.0 (3)C38—C39—H39119.5
C74—C73—C78118.5 (3)C40—C39—H39119.5
C74—C73—C72120.2 (3)C75—C76—C77120.2 (3)
C78—C73—C72121.3 (3)C75—C76—H76119.9
C44—C43—S5122.6 (2)C77—C76—H76119.9
C44—C43—S6121.9 (2)C34—C35—C36120.5 (3)
S5—C43—S6115.58 (19)C34—C35—H35119.8
C46—C47—C48119.4 (3)C36—C35—H35119.8
C46—C47—H47120.3C14—C15—C16120.1 (3)
C48—C47—H47120.3C14—C15—H15119.9
C15—C16—C11119.6 (3)C16—C15—H15119.9
C15—C16—H16120.2C63—C62—C61119.8 (3)
C11—C16—H16120.2C63—C62—H62120.1
C5—C4—C3120.6 (3)C61—C62—H62120.1
C5—C4—S2123.4 (3)C35—C34—C33119.7 (3)
C3—C4—S2116.1 (3)C35—C34—H34120.2
C74—C75—C76120.0 (4)C33—C34—H34120.2
C74—C75—H75120.0C55—C56—C57119.4 (3)
C76—C75—H75120.0C55—C56—H56120.3
C63—C64—C59120.1 (3)C57—C56—H56120.3
C63—C64—H64119.9C18—C19—C20120.7 (3)
C59—C64—H64119.9C18—C19—H19119.7
C3—C8—C7119.2 (3)C20—C19—H19119.7
C3—C8—H8120.4C58—C57—C56120.3 (4)
C7—C8—H8120.4C58—C57—H57119.8
C60—C59—C64119.0 (3)C56—C57—H57119.8
C60—C59—C51121.6 (3)C82—C83—C84120.7 (4)
C64—C59—C51119.3 (3)C82—C83—H83119.7
C17—C22—C21120.1 (3)C84—C83—H83119.7
C17—C22—H22120.0C79—C84—C83119.5 (4)
C21—C22—H22120.0C79—C84—H84120.2
C35—C36—C31120.1 (3)C83—C84—H84120.2
C35—C36—H36120.0C83—C82—C81119.8 (4)
C31—C36—H36120.0C83—C82—H82120.1
C25—C24—C23120.3 (3)C81—C82—H82120.1
C25—C24—S4123.1 (3)C19—C20—C21119.3 (3)
C23—C24—S4116.5 (3)C19—C20—H20120.3
C70—C65—C66120.5 (3)C21—C20—H20120.3
C70—C65—S7123.3 (3)C13—C12—C11120.2 (3)
C66—C65—S7116.1 (3)C13—C12—H12119.9
C50—C45—C46120.8 (3)C11—C12—H12119.9
C50—C45—S5122.8 (3)Cl7—C87—Cl9110.8 (2)
C46—C45—S5116.3 (3)Cl7—C87—Cl8110.2 (2)
C19—C18—C17120.6 (3)Cl9—C87—Cl8110.9 (2)
C19—C18—H18119.7Cl7—C87—H87108.3
C17—C18—H18119.7Cl9—C87—H87108.3
N7—C69—C70118.6 (3)Cl8—C87—H87108.3
N7—C69—C68120.5 (3)Cl10—C88—Cl11110.6 (2)
C70—C69—C68120.8 (3)Cl10—C88—Cl12110.5 (2)
C12—C11—C16119.6 (3)Cl11—C88—Cl12110.2 (2)
C12—C11—C10121.5 (3)Cl10—C88—H88108.5
C16—C11—C10118.9 (3)Cl11—C88—H88108.5
C24—C25—C26119.8 (3)Cl12—C88—H88108.5
C24—C25—H25120.1Cl4—C86—Cl5110.6 (2)
C26—C25—H25120.1Cl4—C86—Cl6110.6 (2)
C66—C67—C68119.9 (3)Cl5—C86—Cl6109.8 (2)
C66—C67—H67120.0Cl4—C86—H86108.6
C68—C67—H67120.0Cl5—C86—H86108.6
C23—C28—C27119.2 (3)Cl6—C86—H86108.6
C23—C28—H28120.4Cl3—C85—Cl2110.8 (2)
C27—C28—H28120.4Cl3—C85—Cl1111.0 (2)
N2—C10—C9120.7 (3)Cl2—C85—Cl1109.3 (2)
N2—C10—C11116.1 (3)Cl3—C85—H85108.6
C9—C10—C11123.2 (3)Cl2—C85—H85108.6
C1—C2—S3122.1 (2)Cl1—C85—H85108.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···Cl2i0.932.943.676 (4)137
C85—H85···N2ii0.982.313.233 (5)156
C12—H12···N6iii0.932.613.344 (4)136
C86—H86···N3iv0.982.293.223 (5)158
C88—H88···N8iv0.982.283.199 (5)155
C87—H87···N5v0.982.323.246 (5)157
C60—H60···N1vi0.932.633.392 (5)139
C78—H78···N4vii0.932.623.427 (4)145
C42—H42···N7v0.932.613.358 (4)138
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+1/2, z; (iii) x, y1, z; (iv) x1/2, y1/2, z; (v) x+1/2, y1/2, z; (vi) x1/2, y+1/2, z; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC42H24N4S4·2CHCl3
Mr951.63
Crystal system, space groupMonoclinic, Cc
Temperature (K)100
a, b, c (Å)14.5359 (11), 14.7543 (11), 39.771 (3)
β (°) 97.616 (2)
V3)8454.3 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.64
Crystal size (mm)0.48 × 0.36 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.748, 0.915
No. of measured, independent and
observed [I > 2σ(I)] reflections
43023, 16629, 16092
Rint0.029
(sin θ/λ)max1)0.621
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.109, 1.07
No. of reflections16629
No. of parameters1045
No. of restraints2
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0576P)2 + 12.7425P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.58, 0.66

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···Cl2i0.932.943.676 (4)137.2
C85—H85···N2ii0.982.313.233 (5)155.9
C12—H12···N6iii0.932.613.344 (4)135.9
C86—H86···N3iv0.982.293.223 (5)157.9
C88—H88···N8iv0.982.283.199 (5)155.1
C87—H87···N5v0.982.323.246 (5)156.9
C60—H60···N1vi0.932.633.392 (5)139.3
C78—H78···N4vii0.932.623.427 (4)145.0
C42—H42···N7v0.932.613.358 (4)137.5
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+1/2, z; (iii) x, y1, z; (iv) x1/2, y1/2, z; (v) x+1/2, y1/2, z; (vi) x1/2, y+1/2, z; (vii) x, y+1, z.
 

Acknowledgements

We thank the Department of Science and Technology, Government of India, for financial support (project No. SR/SI/IC-23/2007). The National X-ray Diffractometer facility set up at the University of Hyderabad by the Department of Science and Technology, Government of India, is gratefully acknowledged for providing the crystal data. We are also grateful to the UGC, New Delhi, for providing infrastructure facilities at the University of Hyderabad under a UPE grant. RB and GD thank the CSIR, New Delhi, for their fellowships.

References

First citationBendikov, M., Wudl, F. & Perepichka, D. F. (2004). Chem. Rev. 104, 4891–4945.  Web of Science CrossRef CAS Google Scholar
First citationBolligarla, R. & Das, S. K. (2011). Tetrahedron Lett. 52, 2496–2500.  Web of Science CrossRef CAS Google Scholar
First citationBouguessa, S., Gouasmia, A. K., Golhen, S., Ouahab, L. & Fabre, J. M. (2003). Tetrahedron Lett. 44, 9275–9278.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMas-Torrent, M., Durkut, M., Hadley, P., Ribas, X. & Rovira, C. (2004). J. Am. Chem. Soc. 126, 984–985.  Web of Science CrossRef PubMed CAS Google Scholar
First citationNaraso, Nishida, J., Ando, S., Yamaguchi, J., Itaka, K., Koinuma, H., Tada, H., Tokito, S. & Yamashita, Y. (2005). J. Am. Chem. Soc. 127, 10142–10143.  Web of Science CrossRef CAS Google Scholar
First citationNoda, B., Katsuhara, M., Aoyagi, I., Mori, T., Taguchi, T., Kambayashi, T., Ishikawa, K. & Takezoe, H. (2005). Chem. Lett. 34, 392–393.  Web of Science CrossRef CAS Google Scholar
First citationOtsubo, T. & Takimiya, K. (2004). Bull. Chem. Soc. Jpn, 77, 43–58.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYamada, J. & Sugimoto, T. (2004). In TTF Chemistry, Fundamentals and Application of Tetrathiafulvalene. Berlin: Springer.  Google Scholar

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Volume 67| Part 9| September 2011| Pages o2231-o2232
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