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

Bolligarla, R.; Durgaprasad, G.; Das, S.K.

doi:10.1107/S1600536811029540

organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S1600536811029540

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

Ramababu Bolligarla,^a Gummadi Durgaprasad ^a and Samar K. Das ^a ^*

^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 ). 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

Crystal data

C₄₂H₂₄N₄S₄·2CHCl₃
M_r = 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 ) T_min = 0.748, T_max = 0.915
43023 measured reflections
16629 independent reflections
16092 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯N3^iv	0.98	2.29	3.223 (5)	158
C88—H88⋯N8^iv	0.98	2.28	3.199 (5)	155
C87—H87⋯N5^v	0.98	2.32	3.246 (5)	157
C60—H60⋯N1^vi	0.93	2.63	3.392 (5)	139
C78—H78⋯N4^vii	0.93	2.62	3.427 (4)	145
C42—H42⋯N7^v	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 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029540/ds2113sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029540/ds2113Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029540/ds2113Isup3.cml

checkCIF report

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.

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

	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).
	Fig. 2. The Cl···Cl interactions are between the chloroform solvent molecules to form a one dimensional tape.
	Fig. 3. The formation of the title compound.
	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

C₄₂H₂₄N₄S₄·2CHCl₃	F(000) = 3872
M_r = 951.63	D_x = 1.495 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 8772 reflections
a = 14.5359 (11) Å	θ = 2.3–26.2°
b = 14.7543 (11) Å	µ = 0.64 mm⁻¹
c = 39.771 (3) Å	T = 100 K
β = 97.616 (2)°	Block, brown
V = 8454.3 (11) Å³	0.48 × 0.36 × 0.14 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	16629 independent reflections
Radiation source: fine-focus sealed tube	16092 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 26.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
T_min = 0.748, T_max = 0.915	k = −18→18
43023 measured reflections	l = −48→49

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0576P)² + 12.7425P] where P = (F_o² + 2F_c²)/3
16629 reflections	(Δ/σ)_max = 0.001
1045 parameters	Δρ_max = 0.58 e Å⁻³
2 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₄₂H₂₄N₄S₄·2CHCl₃	V = 8454.3 (11) Å³
M_r = 951.63	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 14.5359 (11) Å	µ = 0.64 mm⁻¹
b = 14.7543 (11) Å	T = 100 K
c = 39.771 (3) Å	0.48 × 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)
T_min = 0.748, T_max = 0.915	R_int = 0.029
43023 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0576P)² + 12.7425P] where P = (F_o² + 2F_c²)/3
16629 reflections	Δρ_max = 0.58 e Å⁻³
1045 parameters	Δρ_min = −0.66 e Å⁻³

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

	x	y	z	U_iso*/U_eq
S5	0.12002 (6)	0.93290 (6)	0.57016 (2)	0.02468 (18)
S4	0.58994 (6)	0.14264 (6)	0.51422 (2)	0.02435 (18)
S8	0.35756 (6)	0.86813 (6)	0.51766 (2)	0.02512 (18)
S1	0.37317 (6)	0.14711 (6)	0.58085 (2)	0.02433 (18)
S7	0.22618 (6)	1.02323 (6)	0.51246 (2)	0.02470 (18)
S3	0.44035 (6)	0.27438 (6)	0.52303 (2)	0.02481 (18)
S6	0.25227 (6)	0.77850 (6)	0.57503 (2)	0.02452 (18)
S2	0.52343 (6)	0.01627 (6)	0.57179 (2)	0.02431 (18)
C68	0.4590 (2)	1.0229 (2)	0.44690 (8)	0.0207 (7)
N7	0.39830 (19)	1.16091 (19)	0.42016 (7)	0.0210 (6)
N3	0.5599 (2)	0.4788 (2)	0.43348 (7)	0.0232 (6)
C17	0.2316 (2)	−0.1369 (2)	0.72103 (8)	0.0195 (7)
C31	0.7318 (2)	0.4258 (2)	0.37375 (8)	0.0209 (7)
N6	0.08049 (19)	0.63969 (19)	0.66733 (7)	0.0208 (6)
C26	0.6392 (2)	0.3373 (2)	0.44750 (8)	0.0207 (7)
N2	0.40713 (19)	−0.18868 (19)	0.66189 (7)	0.0207 (6)
C7	0.3249 (2)	−0.0484 (2)	0.64744 (8)	0.0203 (7)
N4	0.69477 (19)	0.34997 (19)	0.42295 (7)	0.0205 (6)
C80	0.4410 (2)	1.3117 (2)	0.37982 (8)	0.0231 (7)
H80	0.4365	1.3281	0.4021	0.028*
N5	−0.0499 (2)	0.78039 (19)	0.66059 (7)	0.0201 (6)
C49	0.0203 (2)	0.7780 (2)	0.64082 (8)	0.0208 (7)
C27	0.5694 (2)	0.4015 (2)	0.45210 (8)	0.0208 (7)
C3	0.3766 (2)	0.0475 (2)	0.60497 (8)	0.0204 (7)
C72	0.5312 (2)	1.0836 (2)	0.40408 (8)	0.0205 (7)
C53	0.0259 (2)	0.5814 (2)	0.71666 (8)	0.0198 (7)
N8	0.52848 (19)	1.0185 (2)	0.42723 (7)	0.0217 (6)
C70	0.3237 (2)	1.0982 (2)	0.46466 (8)	0.0220 (7)
H70	0.2830	1.1471	0.4633	0.026*
C79	0.4564 (2)	1.2221 (2)	0.37206 (8)	0.0206 (7)
N1	0.27045 (19)	−0.06132 (19)	0.67222 (7)	0.0217 (6)
C48	0.0841 (2)	0.7047 (2)	0.64326 (8)	0.0213 (7)
C5	0.4564 (2)	−0.0944 (2)	0.61861 (8)	0.0214 (7)
H5	0.5013	−0.1366	0.6147	0.026*
C23	0.5161 (2)	0.3050 (2)	0.49429 (8)	0.0215 (7)
C6	0.3965 (2)	−0.1118 (2)	0.64298 (8)	0.0195 (7)
C52	0.0166 (2)	0.6463 (2)	0.68797 (8)	0.0195 (7)
C46	0.1639 (2)	0.7729 (2)	0.60089 (8)	0.0200 (7)
C71	0.4624 (2)	1.1536 (2)	0.39973 (8)	0.0206 (7)
C63	−0.2366 (3)	0.8073 (3)	0.73290 (9)	0.0287 (8)
H63	−0.2555	0.8629	0.7406	0.034*
C37	0.6026 (2)	0.5772 (2)	0.39069 (8)	0.0211 (7)
C73	0.6101 (2)	1.0780 (2)	0.38364 (8)	0.0232 (7)
C43	0.2165 (2)	0.8821 (2)	0.55573 (8)	0.0225 (7)
C47	0.1552 (2)	0.7027 (2)	0.62264 (8)	0.0220 (7)
H47	0.1962	0.6540	0.6238	0.026*
C16	0.4548 (2)	−0.3216 (2)	0.71374 (8)	0.0205 (7)
H16	0.5061	−0.2893	0.7086	0.025*
C4	0.4483 (2)	−0.0150 (2)	0.60068 (8)	0.0194 (6)
C75	0.7122 (3)	0.9879 (3)	0.35420 (10)	0.0292 (8)
H75	0.7312	0.9315	0.3473	0.035*
C64	−0.1626 (2)	0.8035 (2)	0.71444 (9)	0.0244 (7)
H64	−0.1332	0.8566	0.7092	0.029*
C8	0.3153 (2)	0.0312 (2)	0.62766 (8)	0.0216 (7)
H8	0.2679	0.0722	0.6300	0.026*
C59	−0.1318 (2)	0.7194 (2)	0.70355 (8)	0.0198 (7)
C22	0.1364 (2)	−0.1222 (2)	0.71611 (9)	0.0228 (7)
H22	0.1063	−0.1097	0.6945	0.027*
C36	0.8284 (3)	0.4120 (2)	0.37773 (9)	0.0256 (7)
H36	0.8605	0.4017	0.3992	0.031*
C24	0.5876 (2)	0.2414 (2)	0.49009 (8)	0.0205 (7)
C65	0.3148 (2)	1.0287 (2)	0.48684 (8)	0.0207 (7)
C45	0.1000 (2)	0.8464 (2)	0.59820 (8)	0.0215 (7)
C18	0.2760 (3)	−0.1517 (3)	0.75389 (9)	0.0289 (8)
H18	0.3399	−0.1602	0.7575	0.035*
C69	0.3949 (2)	1.0949 (2)	0.44409 (9)	0.0216 (7)
C11	0.3653 (2)	−0.2869 (2)	0.70489 (8)	0.0211 (7)
C25	0.6484 (2)	0.2580 (2)	0.46729 (8)	0.0220 (7)
H25	0.6957	0.2169	0.4649	0.026*
C67	0.4498 (2)	0.9523 (2)	0.47032 (8)	0.0225 (7)
H67	0.4923	0.9049	0.4727	0.027*
C28	0.5076 (2)	0.3840 (2)	0.47621 (8)	0.0219 (7)
H28	0.4618	0.4258	0.4796	0.026*
C10	0.3537 (2)	−0.2001 (2)	0.68596 (8)	0.0210 (7)
C2	0.4958 (2)	0.1718 (2)	0.53564 (8)	0.0217 (7)
C74	0.6393 (2)	0.9941 (2)	0.37293 (9)	0.0251 (7)
H74	0.6092	0.9417	0.3785	0.030*
C51	−0.0528 (2)	0.7167 (2)	0.68359 (8)	0.0208 (7)
C1	0.4669 (2)	0.1187 (2)	0.55954 (8)	0.0225 (7)
C38	0.5142 (2)	0.6136 (2)	0.38140 (9)	0.0252 (7)
H38	0.4622	0.5831	0.3868	0.030*
C30	0.6805 (2)	0.4221 (2)	0.40339 (8)	0.0195 (7)
C78	0.6585 (2)	1.1555 (2)	0.37596 (9)	0.0242 (7)
H78	0.6414	1.2117	0.3837	0.029*
C61	−0.2542 (3)	0.6465 (3)	0.72855 (9)	0.0273 (8)
H61	−0.2862	0.5941	0.7329	0.033*
C29	0.6135 (2)	0.4903 (2)	0.40974 (8)	0.0199 (7)
C60	−0.1785 (2)	0.6410 (2)	0.71077 (8)	0.0227 (7)
H60	−0.1591	0.5849	0.7037	0.027*
C41	0.6691 (3)	0.7090 (3)	0.36691 (9)	0.0266 (8)
H41	0.7210	0.7417	0.3627	0.032*
C54	0.0349 (2)	0.4884 (2)	0.71084 (9)	0.0246 (7)
H54	0.0318	0.4666	0.6888	0.030*
C50	0.0281 (2)	0.8484 (2)	0.61736 (8)	0.0214 (7)
H50	−0.0148	0.8955	0.6149	0.026*
C66	0.3785 (2)	0.9539 (2)	0.48946 (8)	0.0214 (7)
C9	0.2856 (2)	−0.1324 (2)	0.69186 (8)	0.0213 (7)
C40	0.5808 (3)	0.7428 (2)	0.35680 (9)	0.0264 (7)
H40	0.5729	0.7974	0.3451	0.032*
C21	0.0860 (3)	−0.1262 (2)	0.74348 (10)	0.0271 (8)
H21	0.0220	−0.1179	0.7400	0.032*
C58	0.0324 (3)	0.6119 (2)	0.75016 (9)	0.0269 (7)
H58	0.0258	0.6733	0.7545	0.032*
C33	0.7330 (3)	0.4383 (3)	0.31369 (10)	0.0328 (8)
H33	0.7008	0.4460	0.2921	0.039*
C14	0.3904 (3)	−0.4529 (2)	0.73799 (9)	0.0263 (7)
H14	0.3986	−0.5083	0.7491	0.032*
C44	0.2612 (2)	0.9198 (2)	0.53193 (8)	0.0216 (7)
C81	0.4321 (3)	1.3774 (3)	0.35454 (10)	0.0320 (8)
H81	0.4211	1.4375	0.3599	0.038*
C77	0.7313 (3)	1.1497 (3)	0.35712 (10)	0.0308 (8)
H77	0.7629	1.2017	0.3521	0.037*
C42	0.6796 (2)	0.6263 (2)	0.38336 (8)	0.0226 (7)
H42	0.7388	0.6030	0.3896	0.027*
C13	0.3022 (3)	−0.4186 (2)	0.72916 (9)	0.0265 (7)
H13	0.2510	−0.4514	0.7341	0.032*
C32	0.6861 (2)	0.4391 (3)	0.34140 (9)	0.0274 (8)
H32	0.6223	0.4489	0.3384	0.033*
C55	0.0485 (2)	0.4289 (2)	0.73784 (10)	0.0284 (8)
H55	0.0524	0.3671	0.7337	0.034*
C39	0.5040 (3)	0.6944 (2)	0.36430 (9)	0.0280 (8)
H39	0.4447	0.7171	0.3576	0.034*
C76	0.7571 (2)	1.0655 (3)	0.34570 (9)	0.0302 (8)
H76	0.8048	1.0614	0.3323	0.036*
C35	0.8754 (3)	0.4136 (3)	0.34986 (10)	0.0315 (8)
H35	0.9395	0.4063	0.3527	0.038*
C15	0.4667 (2)	−0.4050 (2)	0.73035 (9)	0.0250 (7)
H15	0.5261	−0.4283	0.7363	0.030*
C62	−0.2825 (3)	0.7294 (3)	0.73994 (9)	0.0292 (8)
H62	−0.3325	0.7324	0.7523	0.035*
C34	0.8282 (3)	0.4260 (3)	0.31783 (10)	0.0322 (8)
H34	0.8602	0.4261	0.2991	0.039*
C56	0.0565 (2)	0.4594 (3)	0.77062 (10)	0.0296 (8)
H56	0.0671	0.4188	0.7886	0.036*
C19	0.2261 (3)	−0.1538 (3)	0.78084 (9)	0.0325 (8)
H19	0.2567	−0.1629	0.8026	0.039*
C57	0.0484 (3)	0.5518 (3)	0.77677 (10)	0.0303 (8)
H57	0.0538	0.5730	0.7990	0.036*
C83	0.4533 (3)	1.2638 (3)	0.31343 (10)	0.0340 (9)
H83	0.4572	1.2475	0.2911	0.041*
C84	0.4615 (2)	1.1974 (3)	0.33861 (9)	0.0268 (7)
H84	0.4703	1.1371	0.3331	0.032*
C82	0.4396 (3)	1.3532 (3)	0.32132 (10)	0.0350 (9)
H82	0.4354	1.3971	0.3044	0.042*
C20	0.1307 (3)	−0.1424 (3)	0.77592 (9)	0.0295 (8)
H20	0.0970	−0.1457	0.7942	0.035*
C12	0.2895 (2)	−0.3356 (2)	0.71289 (9)	0.0244 (7)
H12	0.2299	−0.3125	0.7073	0.029*
Cl8	0.19602 (6)	0.45268 (6)	0.64885 (2)	0.03064 (19)
Cl5	−0.10844 (6)	0.22596 (6)	0.44357 (2)	0.0317 (2)
Cl12	0.27482 (6)	0.34015 (6)	0.44034 (2)	0.0313 (2)
Cl3	0.99363 (8)	0.14803 (9)	0.58894 (3)	0.0480 (3)
Cl4	−0.02752 (9)	0.13926 (9)	0.50589 (3)	0.0495 (3)
Cl10	0.22187 (9)	0.41714 (9)	0.50180 (3)	0.0539 (3)
Cl11	0.28527 (8)	0.53372 (7)	0.45119 (4)	0.0497 (3)
Cl9	0.25430 (9)	0.38265 (9)	0.58694 (3)	0.0515 (3)
Cl7	0.18825 (8)	0.26046 (7)	0.63526 (4)	0.0513 (3)
C87	0.2487 (3)	0.3614 (3)	0.63006 (10)	0.0308 (8)
H87	0.3122	0.3547	0.6416	0.037*
C88	0.2241 (3)	0.4340 (3)	0.45824 (10)	0.0310 (8)
H88	0.1601	0.4404	0.4472	0.037*
Cl1	0.88234 (7)	0.06387 (8)	0.63569 (3)	0.0472 (3)
Cl6	0.09042 (8)	0.22708 (8)	0.46238 (4)	0.0553 (3)
C86	−0.0125 (3)	0.1644 (3)	0.46373 (10)	0.0332 (8)
H86	−0.0078	0.1074	0.4515	0.040*
C85	0.9839 (3)	0.1270 (3)	0.63160 (10)	0.0323 (8)
H85	0.9802	0.1852	0.6432	0.039*
Cl2	1.08202 (6)	0.06723 (6)	0.65138 (2)	0.03064 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S5	0.0254 (4)	0.0253 (4)	0.0246 (4)	0.0057 (3)	0.0081 (3)	0.0018 (3)
S4	0.0264 (4)	0.0197 (4)	0.0264 (4)	0.0062 (3)	0.0018 (3)	0.0033 (3)
S8	0.0252 (4)	0.0237 (4)	0.0281 (4)	0.0055 (3)	0.0095 (3)	0.0000 (3)
S1	0.0260 (4)	0.0205 (4)	0.0261 (4)	0.0069 (3)	0.0017 (3)	0.0028 (3)
S7	0.0236 (4)	0.0260 (4)	0.0257 (4)	0.0068 (3)	0.0075 (3)	−0.0012 (3)
S3	0.0269 (4)	0.0226 (4)	0.0253 (4)	0.0067 (3)	0.0050 (3)	0.0049 (3)
S6	0.0220 (4)	0.0259 (4)	0.0268 (4)	0.0045 (3)	0.0075 (3)	−0.0016 (3)
S2	0.0260 (4)	0.0200 (4)	0.0275 (4)	0.0060 (3)	0.0056 (3)	0.0044 (3)
C68	0.0197 (16)	0.0226 (17)	0.0187 (15)	0.0020 (13)	−0.0020 (12)	−0.0048 (12)
N7	0.0194 (14)	0.0232 (15)	0.0193 (14)	0.0027 (11)	−0.0013 (11)	−0.0024 (11)
N3	0.0265 (15)	0.0206 (14)	0.0216 (14)	0.0043 (12)	0.0000 (11)	−0.0013 (11)
C17	0.0227 (16)	0.0140 (15)	0.0219 (16)	0.0014 (12)	0.0030 (13)	−0.0022 (12)
C31	0.0218 (16)	0.0165 (16)	0.0242 (17)	0.0049 (13)	0.0019 (13)	−0.0044 (13)
N6	0.0208 (14)	0.0187 (14)	0.0221 (14)	0.0035 (11)	0.0000 (11)	−0.0028 (11)
C26	0.0206 (16)	0.0203 (16)	0.0206 (16)	0.0004 (13)	0.0007 (12)	−0.0064 (13)
N2	0.0204 (14)	0.0163 (13)	0.0245 (14)	0.0046 (11)	−0.0006 (11)	−0.0006 (11)
C7	0.0205 (16)	0.0200 (16)	0.0194 (15)	0.0028 (13)	−0.0013 (12)	−0.0038 (13)
N4	0.0201 (14)	0.0217 (14)	0.0187 (13)	0.0016 (11)	−0.0013 (11)	−0.0028 (11)
C80	0.0164 (15)	0.0318 (19)	0.0207 (16)	0.0022 (14)	0.0012 (12)	−0.0008 (14)
N5	0.0209 (14)	0.0196 (14)	0.0199 (13)	0.0025 (11)	0.0025 (11)	−0.0013 (11)
C49	0.0174 (15)	0.0261 (18)	0.0185 (15)	0.0052 (13)	0.0005 (12)	−0.0032 (13)
C27	0.0214 (16)	0.0194 (16)	0.0203 (16)	0.0037 (13)	−0.0020 (13)	−0.0017 (13)
C3	0.0254 (17)	0.0160 (16)	0.0179 (15)	0.0038 (13)	−0.0043 (13)	−0.0012 (12)
C72	0.0187 (16)	0.0251 (17)	0.0177 (15)	0.0004 (13)	0.0020 (12)	−0.0073 (13)
C53	0.0138 (15)	0.0217 (17)	0.0234 (16)	0.0037 (12)	0.0010 (12)	−0.0004 (13)
N8	0.0148 (13)	0.0258 (15)	0.0243 (14)	0.0029 (11)	0.0020 (11)	−0.0054 (12)
C70	0.0238 (17)	0.0216 (17)	0.0203 (16)	0.0053 (13)	0.0013 (13)	−0.0045 (13)
C79	0.0131 (15)	0.0232 (17)	0.0248 (16)	−0.0001 (13)	0.0001 (12)	0.0011 (13)
N1	0.0186 (14)	0.0193 (14)	0.0265 (15)	0.0030 (11)	0.0009 (11)	−0.0036 (11)
C48	0.0193 (16)	0.0243 (17)	0.0198 (16)	0.0011 (13)	0.0006 (12)	−0.0042 (13)
C5	0.0198 (16)	0.0194 (16)	0.0240 (17)	0.0047 (13)	−0.0005 (13)	−0.0019 (13)
C23	0.0237 (16)	0.0204 (17)	0.0193 (16)	0.0014 (13)	−0.0012 (13)	−0.0010 (12)
C6	0.0223 (16)	0.0154 (15)	0.0195 (16)	−0.0003 (13)	−0.0023 (13)	−0.0047 (12)
C52	0.0181 (15)	0.0221 (17)	0.0180 (15)	0.0005 (13)	0.0016 (12)	−0.0041 (12)
C46	0.0144 (15)	0.0285 (18)	0.0167 (15)	0.0029 (13)	0.0012 (12)	−0.0054 (13)
C71	0.0162 (15)	0.0222 (17)	0.0220 (16)	0.0005 (13)	−0.0030 (12)	−0.0049 (13)
C63	0.0259 (19)	0.028 (2)	0.032 (2)	0.0086 (15)	0.0062 (15)	−0.0042 (15)
C37	0.0234 (16)	0.0194 (16)	0.0204 (16)	0.0024 (13)	0.0028 (13)	−0.0043 (13)
C73	0.0184 (16)	0.0300 (19)	0.0202 (16)	0.0019 (14)	−0.0007 (13)	−0.0051 (13)
C43	0.0179 (16)	0.0276 (18)	0.0221 (17)	0.0054 (14)	0.0030 (13)	−0.0039 (14)
C47	0.0214 (16)	0.0223 (17)	0.0215 (16)	0.0090 (13)	0.0004 (13)	−0.0017 (13)
C16	0.0220 (16)	0.0161 (16)	0.0237 (17)	0.0016 (13)	0.0040 (13)	−0.0014 (12)
C4	0.0204 (16)	0.0196 (16)	0.0175 (15)	0.0001 (13)	−0.0005 (12)	−0.0024 (12)
C75	0.0248 (18)	0.029 (2)	0.0340 (19)	0.0036 (15)	0.0058 (15)	−0.0063 (15)
C64	0.0197 (16)	0.0250 (18)	0.0280 (18)	0.0034 (14)	0.0018 (13)	0.0016 (14)
C8	0.0206 (16)	0.0193 (16)	0.0246 (16)	0.0081 (13)	0.0016 (13)	−0.0018 (13)
C59	0.0158 (15)	0.0212 (16)	0.0213 (16)	0.0062 (13)	−0.0014 (12)	−0.0011 (13)
C22	0.0214 (17)	0.0158 (16)	0.0301 (18)	0.0043 (13)	−0.0005 (14)	0.0017 (13)
C36	0.0264 (18)	0.0192 (17)	0.0301 (18)	0.0053 (14)	−0.0002 (14)	−0.0031 (14)
C24	0.0226 (16)	0.0154 (16)	0.0222 (16)	0.0004 (13)	−0.0010 (13)	−0.0009 (12)
C65	0.0189 (16)	0.0251 (18)	0.0181 (16)	0.0003 (13)	0.0015 (12)	−0.0048 (13)
C45	0.0228 (17)	0.0233 (17)	0.0176 (15)	0.0014 (13)	−0.0001 (13)	−0.0022 (13)
C18	0.0210 (17)	0.038 (2)	0.0279 (18)	0.0074 (15)	0.0023 (14)	−0.0026 (16)
C69	0.0194 (16)	0.0218 (17)	0.0228 (16)	0.0044 (13)	−0.0003 (12)	−0.0050 (13)
C11	0.0255 (17)	0.0207 (17)	0.0163 (15)	0.0032 (13)	−0.0005 (13)	−0.0028 (12)
C25	0.0238 (17)	0.0187 (16)	0.0218 (17)	0.0055 (13)	−0.0028 (13)	−0.0004 (13)
C67	0.0196 (16)	0.0234 (17)	0.0239 (17)	0.0051 (13)	0.0012 (13)	−0.0030 (13)
C28	0.0213 (16)	0.0212 (17)	0.0229 (17)	0.0064 (14)	0.0017 (13)	−0.0021 (13)
C10	0.0201 (16)	0.0185 (16)	0.0229 (17)	0.0039 (13)	−0.0023 (13)	−0.0061 (13)
C2	0.0243 (16)	0.0174 (16)	0.0225 (16)	0.0077 (13)	−0.0009 (13)	−0.0006 (12)
C74	0.0211 (17)	0.0235 (18)	0.0308 (18)	0.0012 (14)	0.0036 (14)	−0.0028 (14)
C51	0.0175 (16)	0.0248 (17)	0.0192 (16)	0.0018 (13)	−0.0017 (12)	−0.0045 (13)
C1	0.0248 (17)	0.0195 (17)	0.0219 (16)	0.0047 (14)	−0.0015 (13)	−0.0012 (13)
C38	0.0252 (18)	0.0240 (18)	0.0274 (18)	−0.0007 (14)	0.0066 (14)	0.0003 (14)
C30	0.0178 (15)	0.0174 (16)	0.0223 (16)	0.0023 (12)	−0.0013 (12)	−0.0046 (12)
C78	0.0210 (17)	0.0212 (18)	0.0297 (18)	0.0029 (14)	0.0007 (14)	−0.0052 (14)
C61	0.0250 (18)	0.0298 (19)	0.0263 (18)	−0.0002 (15)	0.0008 (14)	0.0062 (14)
C29	0.0200 (16)	0.0220 (17)	0.0169 (15)	0.0012 (13)	−0.0007 (12)	−0.0025 (13)
C60	0.0209 (16)	0.0274 (18)	0.0187 (16)	0.0064 (14)	−0.0018 (13)	−0.0006 (13)
C41	0.0289 (19)	0.0271 (18)	0.0240 (17)	−0.0015 (15)	0.0045 (14)	−0.0040 (14)
C54	0.0183 (16)	0.0246 (18)	0.0311 (18)	0.0041 (14)	0.0036 (14)	−0.0048 (14)
C50	0.0205 (16)	0.0258 (18)	0.0175 (15)	0.0056 (13)	0.0007 (12)	−0.0020 (13)
C66	0.0189 (16)	0.0238 (17)	0.0202 (16)	0.0025 (13)	−0.0027 (12)	−0.0026 (13)
C9	0.0190 (16)	0.0220 (17)	0.0216 (16)	0.0013 (13)	−0.0015 (13)	−0.0018 (13)
C40	0.036 (2)	0.0211 (17)	0.0224 (17)	0.0044 (15)	0.0046 (15)	0.0032 (13)
C21	0.0225 (17)	0.0210 (17)	0.038 (2)	0.0045 (14)	0.0061 (15)	−0.0005 (15)
C58	0.0288 (18)	0.0223 (18)	0.0285 (18)	0.0059 (14)	0.0000 (14)	−0.0040 (14)
C33	0.0308 (19)	0.044 (2)	0.0239 (18)	0.0059 (17)	0.0039 (15)	−0.0037 (16)
C14	0.038 (2)	0.0162 (16)	0.0250 (18)	0.0048 (14)	0.0034 (15)	0.0006 (13)
C44	0.0205 (16)	0.0234 (17)	0.0208 (16)	0.0067 (13)	0.0022 (13)	−0.0056 (13)
C81	0.0241 (18)	0.0251 (19)	0.045 (2)	0.0022 (15)	−0.0006 (16)	0.0037 (16)
C77	0.0231 (18)	0.030 (2)	0.040 (2)	−0.0013 (15)	0.0053 (15)	0.0027 (16)
C42	0.0238 (17)	0.0247 (18)	0.0188 (16)	0.0035 (14)	0.0018 (13)	−0.0063 (13)
C13	0.0262 (18)	0.0212 (17)	0.0326 (19)	−0.0046 (14)	0.0064 (15)	−0.0034 (14)
C32	0.0212 (17)	0.032 (2)	0.0290 (18)	0.0043 (14)	0.0017 (14)	−0.0069 (15)
C55	0.0209 (17)	0.0177 (17)	0.046 (2)	0.0041 (13)	0.0032 (15)	0.0028 (15)
C39	0.0285 (18)	0.0241 (18)	0.0306 (19)	0.0090 (15)	0.0012 (15)	0.0013 (14)
C76	0.0187 (16)	0.044 (2)	0.0300 (19)	0.0001 (15)	0.0093 (14)	−0.0029 (16)
C35	0.0211 (18)	0.030 (2)	0.045 (2)	0.0027 (15)	0.0098 (16)	−0.0022 (16)
C15	0.0247 (17)	0.0222 (17)	0.0271 (18)	0.0094 (14)	−0.0003 (14)	−0.0001 (14)
C62	0.0242 (18)	0.038 (2)	0.0263 (18)	0.0062 (16)	0.0087 (14)	0.0010 (15)
C34	0.037 (2)	0.034 (2)	0.0293 (19)	0.0047 (16)	0.0155 (16)	0.0006 (15)
C56	0.0245 (18)	0.0292 (19)	0.036 (2)	0.0063 (15)	0.0068 (15)	0.0086 (15)
C19	0.034 (2)	0.044 (2)	0.0191 (17)	0.0087 (17)	0.0033 (14)	−0.0009 (15)
C57	0.035 (2)	0.0302 (19)	0.0262 (18)	0.0031 (16)	0.0038 (15)	−0.0011 (15)
C83	0.032 (2)	0.046 (2)	0.0235 (18)	−0.0090 (17)	0.0003 (15)	0.0016 (16)
C84	0.0222 (16)	0.0299 (19)	0.0282 (18)	−0.0025 (14)	0.0025 (14)	−0.0058 (15)
C82	0.028 (2)	0.042 (2)	0.033 (2)	−0.0046 (17)	−0.0042 (15)	0.0110 (17)
C20	0.0295 (19)	0.033 (2)	0.0285 (19)	0.0038 (16)	0.0115 (15)	0.0007 (15)
C12	0.0228 (17)	0.0215 (17)	0.0278 (18)	0.0019 (14)	−0.0006 (14)	−0.0040 (14)
Cl8	0.0284 (4)	0.0303 (5)	0.0336 (5)	0.0075 (4)	0.0059 (4)	−0.0005 (4)
Cl5	0.0323 (5)	0.0290 (5)	0.0348 (5)	0.0064 (4)	0.0081 (4)	0.0012 (4)
Cl12	0.0303 (5)	0.0274 (4)	0.0369 (5)	0.0039 (4)	0.0065 (4)	−0.0034 (4)
Cl3	0.0526 (6)	0.0589 (7)	0.0309 (5)	0.0177 (5)	−0.0004 (5)	−0.0042 (5)
Cl4	0.0617 (7)	0.0542 (7)	0.0312 (5)	0.0169 (6)	0.0012 (5)	−0.0016 (5)
Cl10	0.0671 (8)	0.0633 (8)	0.0297 (5)	0.0260 (6)	0.0004 (5)	−0.0062 (5)
Cl11	0.0380 (6)	0.0282 (5)	0.0789 (8)	0.0028 (4)	−0.0071 (5)	−0.0001 (5)
Cl9	0.0672 (8)	0.0572 (7)	0.0292 (5)	0.0254 (6)	0.0032 (5)	−0.0019 (5)
Cl7	0.0368 (6)	0.0286 (5)	0.0854 (9)	0.0058 (4)	−0.0036 (6)	−0.0016 (5)
C87	0.032 (2)	0.0295 (19)	0.0300 (19)	0.0103 (16)	−0.0002 (15)	0.0013 (15)
C88	0.0272 (19)	0.0308 (19)	0.033 (2)	0.0077 (16)	−0.0043 (15)	−0.0030 (16)
Cl1	0.0266 (5)	0.0371 (6)	0.0780 (8)	0.0024 (4)	0.0067 (5)	−0.0134 (5)
Cl6	0.0304 (5)	0.0353 (6)	0.1000 (10)	0.0036 (4)	0.0084 (6)	−0.0069 (6)
C86	0.0301 (19)	0.031 (2)	0.039 (2)	0.0061 (16)	0.0042 (16)	−0.0035 (16)
C85	0.030 (2)	0.031 (2)	0.036 (2)	0.0109 (16)	0.0018 (16)	−0.0056 (16)
Cl2	0.0274 (4)	0.0296 (5)	0.0350 (5)	0.0050 (4)	0.0044 (4)	−0.0001 (4)

Geometric parameters (Å, º) top

S5—C45	1.745 (4)	C59—C51	1.480 (5)
S5—C43	1.753 (3)	C22—C21	1.392 (5)
S4—C24	1.743 (3)	C22—H22	0.9300
S4—C2	1.759 (4)	C36—C35	1.377 (5)
S8—C66	1.744 (4)	C36—H36	0.9300
S8—C44	1.754 (3)	C24—C25	1.370 (5)
S1—C1	1.748 (4)	C65—C66	1.435 (5)
S1—C3	1.752 (3)	C45—C50	1.373 (5)
S7—C65	1.748 (3)	C18—C19	1.372 (5)
S7—C44	1.755 (4)	C18—H18	0.9300
S3—C23	1.748 (3)	C11—C12	1.388 (5)
S3—C2	1.756 (3)	C11—C10	1.484 (5)
S6—C46	1.751 (3)	C25—H25	0.9300
S6—C43	1.758 (4)	C67—C66	1.365 (5)
S2—C4	1.749 (3)	C67—H67	0.9300
S2—C1	1.758 (3)	C28—H28	0.9300
C68—N8	1.358 (4)	C10—C9	1.447 (5)
C68—C69	1.409 (5)	C2—C1	1.341 (5)
C68—C67	1.415 (5)	C74—H74	0.9300
N7—C71	1.319 (4)	C38—C39	1.370 (5)
N7—C69	1.367 (4)	C38—H38	0.9300
N3—C29	1.312 (4)	C30—C29	1.447 (5)
N3—C27	1.358 (4)	C78—C77	1.377 (5)
C17—C22	1.389 (5)	C78—H78	0.9300
C17—C18	1.396 (5)	C61—C60	1.386 (5)
C17—C9	1.486 (5)	C61—C62	1.386 (5)
C31—C32	1.382 (5)	C61—H61	0.9300
C31—C36	1.406 (5)	C60—H60	0.9300
C31—C30	1.477 (5)	C41—C42	1.383 (5)
N6—C52	1.322 (4)	C41—C40	1.387 (5)
N6—C48	1.361 (4)	C41—H41	0.9300
C26—N4	1.360 (4)	C54—C55	1.380 (5)
C26—C25	1.407 (5)	C54—H54	0.9300
C26—C27	1.417 (5)	C50—H50	0.9300
N2—C10	1.321 (5)	C40—C39	1.391 (5)
N2—C6	1.358 (4)	C40—H40	0.9300
C7—N1	1.356 (4)	C21—C20	1.387 (5)
C7—C8	1.410 (5)	C21—H21	0.9300
C7—C6	1.428 (5)	C58—C57	1.377 (5)
N4—C30	1.318 (4)	C58—H58	0.9300
C80—C79	1.383 (5)	C33—C32	1.371 (5)
C80—C81	1.391 (5)	C33—C34	1.384 (6)
C80—H80	0.9300	C33—H33	0.9300
N5—C51	1.316 (4)	C14—C13	1.380 (5)
N5—C49	1.368 (4)	C14—C15	1.382 (5)
C49—C50	1.412 (5)	C14—H14	0.9300
C49—C48	1.419 (5)	C81—C82	1.387 (6)
C27—C28	1.422 (5)	C81—H81	0.9300
C3—C8	1.371 (5)	C77—C76	1.392 (6)
C3—C4	1.419 (5)	C77—H77	0.9300
C72—N8	1.335 (5)	C42—H42	0.9300
C72—C71	1.433 (5)	C13—C12	1.386 (5)
C72—C73	1.493 (5)	C13—H13	0.9300
C53—C58	1.397 (5)	C32—H32	0.9300
C53—C54	1.402 (5)	C55—C56	1.370 (6)
C53—C52	1.482 (5)	C55—H55	0.9300
C70—C65	1.370 (5)	C39—H39	0.9300
C70—C69	1.402 (5)	C76—H76	0.9300
C70—H70	0.9300	C35—C34	1.377 (6)
C79—C84	1.391 (5)	C35—H35	0.9300
C79—C71	1.488 (5)	C15—H15	0.9300
N1—C9	1.309 (4)	C62—H62	0.9300
C48—C47	1.403 (5)	C34—H34	0.9300
C5—C4	1.367 (5)	C56—C57	1.392 (5)
C5—C6	1.411 (5)	C56—H56	0.9300
C5—H5	0.9300	C19—C20	1.384 (6)
C23—C28	1.367 (5)	C19—H19	0.9300
C23—C24	1.426 (5)	C57—H57	0.9300
C52—C51	1.443 (5)	C83—C82	1.376 (6)
C46—C47	1.365 (5)	C83—C84	1.395 (5)
C46—C45	1.422 (5)	C83—H83	0.9300
C63—C62	1.376 (6)	C84—H84	0.9300
C63—C64	1.381 (5)	C82—H82	0.9300
C63—H63	0.9300	C20—H20	0.9300
C37—C42	1.396 (5)	C12—H12	0.9300
C37—C38	1.397 (5)	Cl8—C87	1.764 (4)
C37—C29	1.486 (5)	Cl5—C86	1.765 (4)
C73—C74	1.393 (5)	Cl12—C88	1.762 (4)
C73—C78	1.397 (5)	Cl3—C85	1.749 (4)
C43—C44	1.338 (5)	Cl4—C86	1.759 (4)
C47—H47	0.9300	Cl10—C88	1.755 (4)
C16—C15	1.396 (5)	Cl11—C88	1.760 (4)
C16—C11	1.398 (5)	Cl9—C87	1.756 (4)
C16—H16	0.9300	Cl7—C87	1.755 (4)
C75—C74	1.377 (5)	C87—H87	0.9800
C75—C76	1.381 (6)	C88—H88	0.9800
C75—H75	0.9300	Cl1—C85	1.771 (4)
C64—C59	1.407 (5)	Cl6—C86	1.765 (4)
C64—H64	0.9300	C86—H86	0.9800
C8—H8	0.9300	C85—Cl2	1.770 (4)
C59—C60	1.391 (5)	C85—H85	0.9800

C45—S5—C43	96.02 (17)	C1—C2—S4	122.5 (2)
C24—S4—C2	95.88 (16)	S3—C2—S4	115.43 (19)
C66—S8—C44	96.17 (16)	C75—C74—C73	120.8 (3)
C1—S1—C3	95.57 (16)	C75—C74—H74	119.6
C65—S7—C44	95.98 (16)	C73—C74—H74	119.6
C23—S3—C2	96.00 (16)	N5—C51—C52	120.7 (3)
C46—S6—C43	95.76 (16)	N5—C51—C59	117.0 (3)
C4—S2—C1	95.70 (16)	C52—C51—C59	122.3 (3)
N8—C68—C69	121.7 (3)	C2—C1—S1	122.7 (2)
N8—C68—C67	119.1 (3)	C2—C1—S2	121.3 (2)
C69—C68—C67	119.2 (3)	S1—C1—S2	115.9 (2)
C71—N7—C69	117.7 (3)	C39—C38—C37	120.1 (3)
C29—N3—C27	118.3 (3)	C39—C38—H38	119.9
C22—C17—C18	119.0 (3)	C37—C38—H38	119.9
C22—C17—C9	120.2 (3)	N4—C30—C29	121.0 (3)
C18—C17—C9	120.8 (3)	N4—C30—C31	116.4 (3)
C32—C31—C36	118.4 (3)	C29—C30—C31	122.4 (3)
C32—C31—C30	121.1 (3)	C77—C78—C73	120.9 (3)
C36—C31—C30	120.4 (3)	C77—C78—H78	119.6
C52—N6—C48	118.7 (3)	C73—C78—H78	119.6
N4—C26—C25	119.6 (3)	C60—C61—C62	120.6 (3)
N4—C26—C27	120.3 (3)	C60—C61—H61	119.7
C25—C26—C27	120.0 (3)	C62—C61—H61	119.7
C10—N2—C6	118.2 (3)	N3—C29—C30	120.9 (3)
N1—C7—C8	119.9 (3)	N3—C29—C37	116.4 (3)
N1—C7—C6	120.2 (3)	C30—C29—C37	122.7 (3)
C8—C7—C6	119.8 (3)	C61—C60—C59	119.9 (3)
C30—N4—C26	118.2 (3)	C61—C60—H60	120.0
C79—C80—C81	120.5 (3)	C59—C60—H60	120.0
C79—C80—H80	119.7	C42—C41—C40	119.6 (3)
C81—C80—H80	119.7	C42—C41—H41	120.2
C51—N5—C49	118.5 (3)	C40—C41—H41	120.2
N5—C49—C50	119.5 (3)	C55—C54—C53	120.1 (3)
N5—C49—C48	120.7 (3)	C55—C54—H54	120.0
C50—C49—C48	119.8 (3)	C53—C54—H54	120.0
N3—C27—C26	121.0 (3)	C45—C50—C49	119.0 (3)
N3—C27—C28	119.5 (3)	C45—C50—H50	120.5
C26—C27—C28	119.5 (3)	C49—C50—H50	120.5
C8—C3—C4	121.1 (3)	C67—C66—C65	120.2 (3)
C8—C3—S1	122.3 (3)	C67—C66—S8	123.8 (3)
C4—C3—S1	116.6 (3)	C65—C66—S8	116.0 (2)
N8—C72—C71	121.2 (3)	N1—C9—C10	121.4 (3)
N8—C72—C73	115.5 (3)	N1—C9—C17	115.9 (3)
C71—C72—C73	123.3 (3)	C10—C9—C17	122.6 (3)
C58—C53—C54	118.5 (3)	C41—C40—C39	119.4 (3)
C58—C53—C52	120.9 (3)	C41—C40—H40	120.3
C54—C53—C52	120.5 (3)	C39—C40—H40	120.3
C72—N8—C68	117.1 (3)	C20—C21—C22	120.3 (3)
C65—C70—C69	119.3 (3)	C20—C21—H21	119.8
C65—C70—H70	120.4	C22—C21—H21	119.8
C69—C70—H70	120.4	C57—C58—C53	120.6 (3)
C80—C79—C84	119.6 (3)	C57—C58—H58	119.7
C80—C79—C71	118.7 (3)	C53—C58—H58	119.7
C84—C79—C71	121.6 (3)	C32—C33—C34	120.1 (4)
C9—N1—C7	118.5 (3)	C32—C33—H33	119.9
N6—C48—C47	119.8 (3)	C34—C33—H33	119.9
N6—C48—C49	120.0 (3)	C13—C14—C15	120.1 (3)
C47—C48—C49	120.1 (3)	C13—C14—H14	119.9
C4—C5—C6	119.7 (3)	C15—C14—H14	119.9
C4—C5—H5	120.1	C43—C44—S8	122.1 (2)
C6—C5—H5	120.1	C43—C44—S7	122.3 (2)
C28—C23—C24	121.1 (3)	S8—C44—S7	115.6 (2)
C28—C23—S3	122.9 (3)	C82—C81—C80	119.8 (4)
C24—C23—S3	116.0 (3)	C82—C81—H81	120.1
N2—C6—C5	119.8 (3)	C80—C81—H81	120.1
N2—C6—C7	120.7 (3)	C78—C77—C76	119.6 (3)
C5—C6—C7	119.5 (3)	C78—C77—H77	120.2
N6—C52—C51	121.0 (3)	C76—C77—H77	120.2
N6—C52—C53	115.5 (3)	C41—C42—C37	121.0 (3)
C51—C52—C53	123.3 (3)	C41—C42—H42	119.5
C47—C46—C45	120.8 (3)	C37—C42—H42	119.5
C47—C46—S6	123.0 (3)	C14—C13—C12	120.3 (3)
C45—C46—S6	116.3 (3)	C14—C13—H13	119.9
N7—C71—C72	121.6 (3)	C12—C13—H13	119.9
N7—C71—C79	115.0 (3)	C33—C32—C31	121.2 (3)
C72—C71—C79	123.4 (3)	C33—C32—H32	119.4
C62—C63—C64	120.5 (3)	C31—C32—H32	119.4
C62—C63—H63	119.8	C56—C55—C54	121.1 (3)
C64—C63—H63	119.8	C56—C55—H55	119.4
C42—C37—C38	118.7 (3)	C54—C55—H55	119.4
C42—C37—C29	121.3 (3)	C38—C39—C40	121.1 (3)
C38—C37—C29	120.0 (3)	C38—C39—H39	119.5
C74—C73—C78	118.5 (3)	C40—C39—H39	119.5
C74—C73—C72	120.2 (3)	C75—C76—C77	120.2 (3)
C78—C73—C72	121.3 (3)	C75—C76—H76	119.9
C44—C43—S5	122.6 (2)	C77—C76—H76	119.9
C44—C43—S6	121.9 (2)	C34—C35—C36	120.5 (3)
S5—C43—S6	115.58 (19)	C34—C35—H35	119.8
C46—C47—C48	119.4 (3)	C36—C35—H35	119.8
C46—C47—H47	120.3	C14—C15—C16	120.1 (3)
C48—C47—H47	120.3	C14—C15—H15	119.9
C15—C16—C11	119.6 (3)	C16—C15—H15	119.9
C15—C16—H16	120.2	C63—C62—C61	119.8 (3)
C11—C16—H16	120.2	C63—C62—H62	120.1
C5—C4—C3	120.6 (3)	C61—C62—H62	120.1
C5—C4—S2	123.4 (3)	C35—C34—C33	119.7 (3)
C3—C4—S2	116.1 (3)	C35—C34—H34	120.2
C74—C75—C76	120.0 (4)	C33—C34—H34	120.2
C74—C75—H75	120.0	C55—C56—C57	119.4 (3)
C76—C75—H75	120.0	C55—C56—H56	120.3
C63—C64—C59	120.1 (3)	C57—C56—H56	120.3
C63—C64—H64	119.9	C18—C19—C20	120.7 (3)
C59—C64—H64	119.9	C18—C19—H19	119.7
C3—C8—C7	119.2 (3)	C20—C19—H19	119.7
C3—C8—H8	120.4	C58—C57—C56	120.3 (4)
C7—C8—H8	120.4	C58—C57—H57	119.8
C60—C59—C64	119.0 (3)	C56—C57—H57	119.8
C60—C59—C51	121.6 (3)	C82—C83—C84	120.7 (4)
C64—C59—C51	119.3 (3)	C82—C83—H83	119.7
C17—C22—C21	120.1 (3)	C84—C83—H83	119.7
C17—C22—H22	120.0	C79—C84—C83	119.5 (4)
C21—C22—H22	120.0	C79—C84—H84	120.2
C35—C36—C31	120.1 (3)	C83—C84—H84	120.2
C35—C36—H36	120.0	C83—C82—C81	119.8 (4)
C31—C36—H36	120.0	C83—C82—H82	120.1
C25—C24—C23	120.3 (3)	C81—C82—H82	120.1
C25—C24—S4	123.1 (3)	C19—C20—C21	119.3 (3)
C23—C24—S4	116.5 (3)	C19—C20—H20	120.3
C70—C65—C66	120.5 (3)	C21—C20—H20	120.3
C70—C65—S7	123.3 (3)	C13—C12—C11	120.2 (3)
C66—C65—S7	116.1 (3)	C13—C12—H12	119.9
C50—C45—C46	120.8 (3)	C11—C12—H12	119.9
C50—C45—S5	122.8 (3)	Cl7—C87—Cl9	110.8 (2)
C46—C45—S5	116.3 (3)	Cl7—C87—Cl8	110.2 (2)
C19—C18—C17	120.6 (3)	Cl9—C87—Cl8	110.9 (2)
C19—C18—H18	119.7	Cl7—C87—H87	108.3
C17—C18—H18	119.7	Cl9—C87—H87	108.3
N7—C69—C70	118.6 (3)	Cl8—C87—H87	108.3
N7—C69—C68	120.5 (3)	Cl10—C88—Cl11	110.6 (2)
C70—C69—C68	120.8 (3)	Cl10—C88—Cl12	110.5 (2)
C12—C11—C16	119.6 (3)	Cl11—C88—Cl12	110.2 (2)
C12—C11—C10	121.5 (3)	Cl10—C88—H88	108.5
C16—C11—C10	118.9 (3)	Cl11—C88—H88	108.5
C24—C25—C26	119.8 (3)	Cl12—C88—H88	108.5
C24—C25—H25	120.1	Cl4—C86—Cl5	110.6 (2)
C26—C25—H25	120.1	Cl4—C86—Cl6	110.6 (2)
C66—C67—C68	119.9 (3)	Cl5—C86—Cl6	109.8 (2)
C66—C67—H67	120.0	Cl4—C86—H86	108.6
C68—C67—H67	120.0	Cl5—C86—H86	108.6
C23—C28—C27	119.2 (3)	Cl6—C86—H86	108.6
C23—C28—H28	120.4	Cl3—C85—Cl2	110.8 (2)
C27—C28—H28	120.4	Cl3—C85—Cl1	111.0 (2)
N2—C10—C9	120.7 (3)	Cl2—C85—Cl1	109.3 (2)
N2—C10—C11	116.1 (3)	Cl3—C85—H85	108.6
C9—C10—C11	123.2 (3)	Cl2—C85—H85	108.6
C1—C2—S3	122.1 (2)	Cl1—C85—H85	108.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···N3^iv	0.98	2.29	3.223 (5)	158
C88—H88···N8^iv	0.98	2.28	3.199 (5)	155
C87—H87···N5^v	0.98	2.32	3.246 (5)	157
C60—H60···N1^vi	0.93	2.63	3.392 (5)	139
C78—H78···N4^vii	0.93	2.62	3.427 (4)	145
C42—H42···N7^v	0.93	2.61	3.358 (4)	138

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, y+1/2, z; (iii) x, y−1, z; (iv) x−1/2, y−1/2, z; (v) x+1/2, y−1/2, z; (vi) x−1/2, y+1/2, z; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₄₂H₂₄N₄S₄·2CHCl₃
M_r	951.63
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	14.5359 (11), 14.7543 (11), 39.771 (3)
β (°)	97.616 (2)
V (Å³)	8454.3 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.48 × 0.36 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.748, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	43023, 16629, 16092
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.621

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.07
No. of reflections	16629
No. of parameters	1045
No. of restraints	2
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0576P)² + 12.7425P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl2ⁱ	0.93	2.94	3.676 (4)	137.2
C85—H85···N2ⁱⁱ	0.98	2.31	3.233 (5)	155.9
C12—H12···N6ⁱⁱⁱ	0.93	2.61	3.344 (4)	135.9
C86—H86···N3^iv	0.98	2.29	3.223 (5)	157.9
C88—H88···N8^iv	0.98	2.28	3.199 (5)	155.1
C87—H87···N5^v	0.98	2.32	3.246 (5)	156.9
C60—H60···N1^vi	0.93	2.63	3.392 (5)	139.3
C78—H78···N4^vii	0.93	2.62	3.427 (4)	145.0
C42—H42···N7^v	0.93	2.61	3.358 (4)	137.5

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, y+1/2, z; (iii) x, y−1, z; (iv) x−1/2, y−1/2, z; (v) x+1/2, y−1/2, z; (vi) x−1/2, 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

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

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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