1,2-Bis{4-[1-(anthracen-9-ylmeth­yl)-1H-1,2,3-triazol-4-yl]phen­yl}-1,2-bis­[4,5-bis­(methyl­sulfan­yl)-1,3-dithiol-2-yl­idene]ethane

Mulla, K.; Zhao, Y.; Dawe, L.N.

doi:10.1107/S1600536812045254

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3298-o3299

doi:10.1107/S1600536812045254

Open

access

1,2-Bis{4-[1-(anthracen-9-ylmethyl)-1H-1,2,3-triazol-4-yl]phenyl}-1,2-bis[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]ethane

Karimulla Mulla,^a Yuming Zhao ^a and Louise N. Dawe ^b ^*

^aDepartment of Chemistry, Memorial University of Newfoundland, St Johns, NL, Canada A1B 3X7, and ^bDepartment of Chemistry and C-CART X-Ray Diffraction Lab, Memorial University of Newfoundland, St Johns, NL, Canada A1B 3X7
^*Correspondence e-mail: louise.dawe@mun.ca

(Received 23 September 2012; accepted 1 November 2012; online 7 November 2012)

The title molecule, C₅₈H₄₄N₆S₈, has point symmetry 2 (in the Schönfliess notation C₂). The related crystallographic twofold axis bisects the central ethane bond while it is parallel to the monoclinic unique axis of the unit cell. The dithiole=C—C=dithiole torsion angle is 103.7 (4)° and the triazole–anthracene moieties adopt a pincer-like conformation. The crystal structure features C—H⋯S and C—H⋯N contacts. The distance between the stacked anthracene fragments [centroid—centroid separations of 3.6871 (19) Å, off-set by 1.516 (3) Å and mean anthracene plane-plane separations of 3.361 (2) Å], which are parallel to (101) and (-101), indicates intermolecular anthracene–anthracene π–π contacts. One of the terminal methylsulfanyl groups was modelled as being disordered with two refined orientations that converged to occupancies of 0.809 (5) and 0.191 (5).

Related literature

The simpler analogues, 4,4′,5,5′-tetramethylthiolato-2,2′-ethanediylidene(1,3-dithiole) and bis(4,5-bis(methylthio)-1,3-dithiol-2-ylidene)succinonitrile, were previously reported by Bryce et al. (1996 ) and Jia et al. (2005 ), respectively. For information on the photophysical properties of tetrathiafulvalene vinylogues, see: Mulla et al. (2012 ). For synthesis via Cu-catalysed alkyne–azide coupling reactions employed for the title compound, see: Meldal & Tornøe (2008 ); Hein et al. (2010 ); Zhao et al. (2012 ). For a discussion of hydrogen bonding, including non-traditional interactions, see: Desiraju (2011 ); Arunan et al. (2011 ). For standard bond lengths, see: Allen et al. (1987 ) and for a description of the Cambridge Structural Database, see Allen (2002 ).

Experimental

Crystal data

C₅₈H₄₄N₆S₈
M_r = 1081.47
Monoclinic, C 2/c
a = 15.906 (4) Å
b = 14.737 (3) Å
c = 21.570 (5) Å
β = 98.846 (7)°
V = 4996 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 168 K
0.27 × 0.23 × 0.12 mm

Data collection

Rigaku AFC8 diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.765, T_max = 0.952
24431 measured reflections
5169 independent reflections
4127 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.160
S = 1.06
5169 reflections
347 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28C⋯N2ⁱ	0.98	2.55	3.495 (5)	161
C25—H25⋯S2ⁱⁱ	0.95	3.00	3.784 (4)	141
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ), publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045254/fb2271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045254/fb2271Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812045254/fb2271Isup3.cml

checkCIF report

Comment top

The asymmetric unit of the title molecule contains a half of the molecule. The whole molecule has the point symmetry 2 (or C₂ in the Schönfliess notation). The twofold axis is parallel to the monoclinic axis and passes through the centre of the C4—C4ⁱ bond (i = -x, y, 1/2 - z; Fig. 1). This point symmetry has been previously reported for the related molecule, bis(4,5-bis(methylthio)-1,3-dithiol-2-ylidene)succinonitrile (Jia et al. 2005). The dithiole═C—C═dithiole torsion angle is 103.7 (4)° for the title molecule, while for the related analogue Jia et al. (2005) reported 91.7° (no reported s.u.). In the Cambridge Crystallographic Database (Allen, 2002), the article by Jia et al. (2005) is deposited as CCDC 285669, refcode JAVWEJ, and the pertinent torsion angle has been given as 85.9 (7)°. The larger value of this torsion angle in the title molecule may result from the adoption of a pincer-like conformation of the triazole and anthracene fragments. Both the title molecule and that reported by Jia et al. (2005) exhibit a twisted cis conformation about the C4—C4ⁱ bond (i = -x, y, 1/2 -z), which contrasts sharply with the planar 2,2'-ethanediylidene(1,3-dithiole) framework reported for 4,4',5,5'-tetramethylthiolato-2,2'-ethanediylidene(1,3-dithiole) (Bryce et al., 1996), which adopts a trans conformation.

One of the terminal S—CH₃ groups was disordered with two refined orientations that converged to occupancy 0.809 (5) for S4, C29 and the attached methyl H atoms H29A, H29B, H29C, and 0.191 (5) for S4A, C29A and the attached methyl H atoms H29D, H29E, H29F. (These hydrogens were difficult to discern in the difference map.)

Non-traditional D–H···A interactions (Arunan et al., 2011, and Desiraju, 2011) are present betweent C25_anthracene—H25···S2ⁱⁱ ((ii) = 1/2 - x, 3/2 - y, 1 - z) and C28_methyl–H28C···N2ⁱⁱⁱ ((iii) = x + 1/2, -y + 3/2, z + 1/2, see Fig. 2 and Table 1). Further intermolecular interactions in the form of π-electron _anthracene—π-electron _anthracene contacts with centroid—centroid separations of 3.6871 (19) Å, off-set by 1.516 (3) Å and mean anthracene plane-plane separations of 3.361 (2) Å are present (Fig. 3; as measured from the anthracene fragment in x, y, z to (iv) = 1/2 - x, 5/2 - y, 1 - z). The molecules that exhibit H-bonding and π-electron—π-electron interactions are parallel to the (1, 0, 1) and (-1, 0, 1) planes (determined using OLEX2 by Dolomanov et al., 2009.)

Related literature top

The simpler analogues, 4,4',5,5'-tetramethylthiolato-2,2'-ethanediylidene(1,3-dithiole) and bis(4,5-bis(methylthio)-1,3-dithiol-2-ylidene)succinonitrile, were previously reported by Bryce et al. (1996) and Jia et al. (2005), respectively. For information on the photophysical properties of tetrathiafulvalene vinylogues, see: Mulla et al. (2012). For synthesis via Cu-catalysed alkyne–azide coupling reactions employed for the title compound, see: Meldal & Tornøe (2008); Hein et al. (2010); Zhao et al. (2012). For a discussion of hydrogen bonding, including non-traditional interactions, see: Desiraju (2011); Arunan et al. (2011). For standard bond lengths, see: Allen et al. (1987) and for a description of the Cambridge Structural Database, see Allen (2002).

Experimental top

The title compound was synthesized by the procedures reported by Mulla et al. (2012). 3 mg of the title compound were added to 0.8 ml of chloroform in a vial and heated to 323 K to give a clear solution. This solution was first cooled to room temperature and then methanol (0.5 ml) was added slowly to the chloroform solution by diffusion at 277 K over 3 days. After this time, yellow prismatic crystals with dimensions similar to those of the measured sample (0.27 × 0.23 × 0.12 mm), formed.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule. The displacement ellipsoids are shown at the 50% probability level. Symmetry code: (i) = -x, y, 1/2 - z.
	Fig. 2. Short C—H···S and C—H···N contacts between the molecules of the title compound. Symmetry codes: (i) -x, y, 1/2 - z; (ii) 1/2 - x, 3/2 - y, 1 - z; (iii) 1/2 + x, 3/2 - y, 1/2 + z.
	Fig. 3. π-electron—π-electron interactions between the anthracene units, propagating parallel to (1, 0, 1), with the centroid-centroid separations of 3.6871 (19) Å (as measured between x, y, z and (iv) = 1/2 - x, 5/2 - y, 1 - z). Symmetry codes: (i) -x, y, 1/2 - z; (iv) 1/2 - x, 5/2 - y, 1 - z; (v) 1/2 + x, 5/2 - y, 1/2 + z; (vi) 1 - x, y, 3/2 - z; (vii) 1 + x, y, 1 + z; (viii) -1/2 + x, 5/2 - y, -1/2 + z; (ix) -1/2 - x, 5/2 - y, -z; (x) -1 + x, y, -1 + z; (xi) -1 - x, y, -1/2 - z.

1,2-Bis{4-[1-(anthracen-9-ylmethyl)-1H-1,2,3-triazol-4-yl]phenyl}- 1,2-bis[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]ethane top

Crystal data top

C₅₈H₄₄N₆S₈	F(000) = 2248
M_r = 1081.47	D_x = 1.438 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 12368 reflections
a = 15.906 (4) Å	θ = 3.3–27.6°
b = 14.737 (3) Å	µ = 0.41 mm⁻¹
c = 21.570 (5) Å	T = 168 K
β = 98.846 (7)°	Prism, yellow
V = 4996 (2) Å³	0.27 × 0.23 × 0.12 mm
Z = 4

Data collection top

Rigaku AFC8 diffractometer	5169 independent reflections
Radiation source: fine-focus sealed tube	4127 reflections with I > 2σ(I)
Graphite - Rigaku SHINE monochromator	R_int = 0.059
Detector resolution: 14.63 pixels mm^-1	θ_max = 26.5°, θ_min = 3.3°
ω scans	h = −19→19
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −18→18
T_min = 0.765, T_max = 0.952	l = −27→24
24431 measured reflections

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)] = 0.058	Hydrogen site location: difference Fourier map
wR(F²) = 0.160	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0767P)² + 8.5759P] where P = (F_o² + 2F_c²)/3
5169 reflections	(Δ/σ)_max < 0.001
347 parameters	Δρ_max = 0.70 e Å⁻³
3 restraints	Δρ_min = −0.62 e Å⁻³
97 constraints

Crystal data top

C₅₈H₄₄N₆S₈	V = 4996 (2) Å³
M_r = 1081.47	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.906 (4) Å	µ = 0.41 mm⁻¹
b = 14.737 (3) Å	T = 168 K
c = 21.570 (5) Å	0.27 × 0.23 × 0.12 mm
β = 98.846 (7)°

Data collection top

Rigaku AFC8 diffractometer	5169 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	4127 reflections with I > 2σ(I)
T_min = 0.765, T_max = 0.952	R_int = 0.059
24431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	3 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.06	Δρ_max = 0.70 e Å⁻³
5169 reflections	Δρ_min = −0.62 e Å⁻³
347 parameters

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.21077 (4)	0.55797 (5)	0.29159 (4)	0.0438 (2)
S2	0.08541 (4)	0.49862 (5)	0.18534 (4)	0.0415 (2)
S3	0.35601 (5)	0.46517 (8)	0.24249 (6)	0.0746 (3)
S4	0.21209 (7)	0.41217 (8)	0.11540 (6)	0.0497 (5)	0.809 (5)
C29	0.2002 (4)	0.2963 (3)	0.1414 (3)	0.0846 (19)	0.809 (5)
H29A	0.2504	0.2791	0.1714	0.127*	0.809 (5)
H29B	0.1943	0.2554	0.1052	0.127*	0.809 (5)
H29C	0.1493	0.2919	0.1618	0.127*	0.809 (5)
S4A	0.2162 (5)	0.3602 (6)	0.1509 (3)	0.086 (3)	0.191 (5)
C29A	0.1999 (15)	0.4153 (16)	0.0740 (10)	0.073 (6)	0.191 (5)
H29D	0.1510	0.4564	0.0711	0.109*	0.191 (5)
H29E	0.1891	0.3691	0.0411	0.109*	0.191 (5)
H29F	0.2508	0.4500	0.0687	0.109*	0.191 (5)
N1	0.11476 (15)	1.01534 (15)	0.50733 (10)	0.0358 (5)
N2	0.1323 (2)	0.95560 (17)	0.55383 (12)	0.0527 (7)
N3	0.1189 (2)	0.87389 (17)	0.52924 (12)	0.0538 (7)
C1	0.10424 (15)	0.56405 (17)	0.25385 (12)	0.0318 (5)
C2	0.24892 (19)	0.4963 (2)	0.23200 (16)	0.0487 (8)
C3	0.1915 (2)	0.4702 (2)	0.18276 (17)	0.0513 (8)
C4	0.04180 (15)	0.61453 (16)	0.27167 (12)	0.0289 (5)
C5	0.05131 (15)	0.67558 (16)	0.32632 (12)	0.0297 (5)
C6	0.11164 (16)	0.66476 (17)	0.38029 (12)	0.0343 (6)
H6	0.1458	0.6115	0.3846	0.041*
C7	0.12316 (17)	0.72875 (18)	0.42735 (13)	0.0366 (6)
H7	0.1642	0.7188	0.4636	0.044*
C8	0.07492 (17)	0.80792 (17)	0.42201 (12)	0.0339 (6)
C9	0.01149 (17)	0.81784 (17)	0.37050 (13)	0.0346 (6)
H9	−0.0235	0.8704	0.3671	0.041*
C10	−0.00144 (16)	0.75248 (17)	0.32412 (12)	0.0319 (5)
H10	−0.0467	0.7596	0.2902	0.038*
C11	0.09216 (17)	0.88302 (18)	0.46645 (12)	0.0360 (6)
C12	0.08963 (17)	0.97300 (18)	0.45269 (13)	0.0371 (6)
H12	0.0734	1.0002	0.4127	0.045*
C13	0.13241 (18)	1.11193 (18)	0.51750 (14)	0.0390 (6)
H13A	0.1583	1.1224	0.5617	0.047*
H13B	0.0787	1.1468	0.5092	0.047*
C14	0.19234 (17)	1.14373 (17)	0.47421 (12)	0.0336 (6)
C15	0.16101 (18)	1.18757 (18)	0.41722 (13)	0.0383 (6)
C16	0.0730 (2)	1.2060 (2)	0.39650 (16)	0.0506 (8)
H16	0.0316	1.1858	0.4207	0.061*
C17	0.0483 (3)	1.2525 (3)	0.34189 (19)	0.0704 (11)
H17	−0.0105	1.2639	0.3289	0.085*
C18	0.1066 (3)	1.2840 (3)	0.30463 (17)	0.0723 (11)
H18	0.0878	1.3185	0.2679	0.087*
C19	0.1897 (3)	1.2648 (3)	0.32130 (15)	0.0641 (10)
H19	0.2291	1.2845	0.2952	0.077*
C20	0.2200 (2)	1.2156 (2)	0.37696 (13)	0.0434 (7)
C21	0.3054 (2)	1.1964 (2)	0.39396 (14)	0.0457 (7)
H21	0.3440	1.2136	0.3665	0.055*
C22	0.33685 (18)	1.15312 (18)	0.44937 (14)	0.0408 (7)
C23	0.4252 (2)	1.1359 (2)	0.46688 (17)	0.0510 (8)
H23	0.4636	1.1531	0.4393	0.061*
C24	0.4557 (2)	1.0955 (2)	0.5221 (2)	0.0609 (10)
H24	0.5152	1.0864	0.5337	0.073*
C25	0.3994 (2)	1.0672 (2)	0.56234 (18)	0.0578 (9)
H25	0.4211	1.0381	0.6008	0.069*
C26	0.3150 (2)	1.08074 (19)	0.54724 (15)	0.0459 (7)
H26	0.2783	1.0599	0.5750	0.055*
C27	0.27920 (17)	1.12572 (17)	0.49037 (13)	0.0359 (6)
C28	0.40626 (19)	0.5551 (3)	0.29117 (17)	0.0573 (9)
H28A	0.3965	0.6131	0.2689	0.086*
H28B	0.4675	0.5435	0.3008	0.086*
H28C	0.3821	0.5578	0.3303	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0279 (3)	0.0485 (4)	0.0533 (5)	0.0072 (3)	0.0005 (3)	−0.0139 (3)
S2	0.0340 (4)	0.0417 (4)	0.0479 (4)	0.0033 (3)	0.0030 (3)	−0.0147 (3)
S3	0.0349 (4)	0.0816 (7)	0.1068 (8)	0.0138 (4)	0.0091 (5)	−0.0313 (6)
S4	0.0565 (7)	0.0525 (8)	0.0425 (9)	0.0104 (5)	0.0157 (5)	−0.0084 (7)
C29	0.121 (5)	0.041 (3)	0.106 (4)	−0.009 (3)	0.061 (4)	−0.033 (3)
S4A	0.108 (5)	0.083 (6)	0.070 (5)	0.044 (4)	0.023 (3)	−0.014 (4)
C29A	0.085 (16)	0.069 (14)	0.067 (16)	0.022 (11)	0.020 (13)	0.023 (13)
N1	0.0426 (12)	0.0321 (11)	0.0351 (12)	−0.0097 (10)	0.0138 (10)	−0.0043 (9)
N2	0.082 (2)	0.0406 (14)	0.0353 (14)	−0.0204 (13)	0.0083 (13)	−0.0019 (11)
N3	0.084 (2)	0.0374 (13)	0.0388 (14)	−0.0203 (13)	0.0053 (13)	0.0008 (11)
C1	0.0282 (12)	0.0273 (12)	0.0395 (14)	−0.0009 (10)	0.0040 (11)	−0.0022 (10)
C2	0.0343 (14)	0.0473 (17)	0.066 (2)	0.0055 (13)	0.0109 (14)	−0.0130 (15)
C3	0.0421 (16)	0.0500 (18)	0.063 (2)	0.0038 (14)	0.0131 (15)	−0.0183 (15)
C4	0.0271 (12)	0.0248 (11)	0.0347 (13)	−0.0013 (9)	0.0046 (10)	0.0015 (10)
C5	0.0296 (12)	0.0255 (12)	0.0349 (13)	−0.0025 (10)	0.0080 (10)	−0.0010 (10)
C6	0.0341 (13)	0.0277 (12)	0.0413 (15)	0.0017 (10)	0.0068 (11)	0.0019 (11)
C7	0.0363 (14)	0.0360 (14)	0.0371 (14)	−0.0040 (11)	0.0036 (11)	0.0009 (11)
C8	0.0383 (14)	0.0285 (12)	0.0371 (14)	−0.0082 (11)	0.0127 (11)	−0.0016 (11)
C9	0.0363 (13)	0.0282 (12)	0.0413 (15)	0.0027 (10)	0.0127 (11)	−0.0002 (11)
C10	0.0301 (12)	0.0320 (13)	0.0348 (13)	0.0002 (10)	0.0085 (10)	−0.0002 (11)
C11	0.0380 (14)	0.0347 (13)	0.0371 (15)	−0.0084 (11)	0.0115 (11)	−0.0029 (11)
C12	0.0422 (15)	0.0350 (14)	0.0353 (14)	−0.0058 (12)	0.0095 (12)	−0.0019 (11)
C13	0.0443 (15)	0.0311 (13)	0.0447 (16)	−0.0080 (12)	0.0166 (13)	−0.0090 (12)
C14	0.0378 (13)	0.0269 (12)	0.0377 (14)	−0.0062 (10)	0.0104 (11)	−0.0053 (11)
C15	0.0425 (15)	0.0304 (13)	0.0417 (15)	−0.0071 (11)	0.0057 (12)	−0.0076 (11)
C16	0.0450 (17)	0.0441 (17)	0.060 (2)	−0.0063 (13)	−0.0006 (15)	−0.0017 (15)
C17	0.061 (2)	0.067 (2)	0.073 (3)	−0.0036 (19)	−0.023 (2)	0.003 (2)
C18	0.086 (3)	0.078 (3)	0.046 (2)	−0.015 (2)	−0.014 (2)	0.0145 (19)
C19	0.086 (3)	0.065 (2)	0.0386 (18)	−0.023 (2)	0.0020 (17)	0.0035 (16)
C20	0.0565 (18)	0.0392 (15)	0.0349 (15)	−0.0153 (13)	0.0080 (13)	−0.0058 (12)
C21	0.0510 (17)	0.0458 (16)	0.0440 (16)	−0.0165 (14)	0.0194 (14)	−0.0092 (13)
C22	0.0410 (15)	0.0325 (13)	0.0512 (17)	−0.0075 (12)	0.0143 (13)	−0.0109 (13)
C23	0.0403 (16)	0.0421 (16)	0.074 (2)	−0.0066 (13)	0.0198 (16)	−0.0111 (16)
C24	0.0382 (16)	0.0437 (18)	0.099 (3)	0.0002 (14)	0.0030 (18)	−0.0094 (19)
C25	0.0546 (19)	0.0392 (16)	0.074 (2)	0.0006 (15)	−0.0084 (17)	0.0083 (16)
C26	0.0473 (16)	0.0346 (14)	0.0541 (18)	−0.0089 (13)	0.0024 (14)	0.0052 (13)
C27	0.0383 (14)	0.0261 (12)	0.0444 (15)	−0.0062 (11)	0.0096 (12)	−0.0051 (11)
C28	0.0326 (15)	0.079 (2)	0.060 (2)	0.0004 (15)	0.0090 (14)	−0.0008 (18)

Geometric parameters (Å, º) top

S1—C2	1.757 (3)	C10—H10	0.9500
S1—C1	1.766 (3)	C11—C12	1.358 (4)
S2—C3	1.747 (3)	C12—H12	0.9500
S2—C1	1.751 (3)	C13—C14	1.508 (4)
S3—C2	1.745 (3)	C13—H13A	0.9900
S3—C28	1.800 (4)	C13—H13B	0.9900
S4—C3	1.760 (3)	C14—C27	1.397 (4)
S4—C29	1.817 (5)	C14—C15	1.410 (4)
C29—H29A	0.9800	C15—C16	1.428 (4)
C29—H29B	0.9800	C15—C20	1.434 (4)
C29—H29C	0.9800	C16—C17	1.367 (5)
S4A—C3	1.827 (7)	C16—H16	0.9500
S4A—C29A	1.829 (16)	C17—C18	1.396 (6)
C29A—H29D	0.9800	C17—H17	0.9500
C29A—H29E	0.9800	C18—C19	1.345 (6)
C29A—H29F	0.9800	C18—H18	0.9500
N1—N2	1.332 (3)	C19—C20	1.421 (5)
N1—C12	1.339 (3)	C19—H19	0.9500
N1—C13	1.461 (3)	C20—C21	1.382 (4)
N2—N3	1.320 (3)	C21—C22	1.379 (4)
N3—C11	1.362 (4)	C21—H21	0.9500
C1—C4	1.343 (3)	C22—C23	1.421 (4)
C2—C3	1.347 (5)	C22—C27	1.427 (4)
C4—C5	1.472 (3)	C23—C24	1.353 (5)
C4—C4ⁱ	1.503 (5)	C23—H23	0.9500
C5—C6	1.399 (4)	C24—C25	1.403 (5)
C5—C10	1.406 (3)	C24—H24	0.9500
C6—C7	1.377 (4)	C25—C26	1.346 (4)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.391 (4)	C26—C27	1.433 (4)
C7—H7	0.9500	C26—H26	0.9500
C8—C9	1.389 (4)	C28—H28A	0.9800
C8—C11	1.462 (4)	C28—H28B	0.9800
C9—C10	1.381 (4)	C28—H28C	0.9800
C9—H9	0.9500

C2—S1—C1	95.96 (14)	N1—C13—C14	109.6 (2)
C3—S2—C1	96.79 (14)	N1—C13—H13A	109.8
C2—S3—C28	102.65 (15)	C14—C13—H13A	109.8
C3—S4—C29	99.2 (2)	N1—C13—H13B	109.8
C3—S4A—C29A	86.5 (9)	C14—C13—H13B	109.8
S4A—C29A—H29D	109.5	H13A—C13—H13B	108.2
S4A—C29A—H29E	109.5	C27—C14—C15	120.5 (2)
H29D—C29A—H29E	109.5	C27—C14—C13	118.8 (3)
S4A—C29A—H29F	109.5	C15—C14—C13	120.6 (3)
H29D—C29A—H29F	109.5	C14—C15—C16	123.9 (3)
H29E—C29A—H29F	109.5	C14—C15—C20	118.9 (3)
N2—N1—C12	110.8 (2)	C16—C15—C20	117.2 (3)
N2—N1—C13	121.2 (2)	C17—C16—C15	120.2 (3)
C12—N1—C13	127.6 (2)	C17—C16—H16	119.9
N3—N2—N1	107.3 (2)	C15—C16—H16	119.9
N2—N3—C11	108.4 (2)	C16—C17—C18	122.3 (4)
C4—C1—S2	120.55 (19)	C16—C17—H17	118.9
C4—C1—S1	126.5 (2)	C18—C17—H17	118.9
S2—C1—S1	112.87 (14)	C19—C18—C17	119.3 (3)
C3—C2—S3	123.9 (2)	C19—C18—H18	120.4
C3—C2—S1	117.1 (2)	C17—C18—H18	120.4
S3—C2—S1	118.77 (19)	C18—C19—C20	121.6 (4)
C2—C3—S2	116.6 (2)	C18—C19—H19	119.2
C2—C3—S4	126.9 (2)	C20—C19—H19	119.2
S2—C3—S4	116.51 (19)	C21—C20—C19	121.4 (3)
C2—C3—S4A	113.0 (3)	C21—C20—C15	119.2 (3)
S2—C3—S4A	119.3 (3)	C19—C20—C15	119.4 (3)
C1—C4—C5	125.3 (2)	C22—C21—C20	122.4 (3)
C1—C4—C4ⁱ	116.4 (2)	C22—C21—H21	118.8
C5—C4—C4ⁱ	118.0 (2)	C20—C21—H21	118.8
C6—C5—C10	116.7 (2)	C21—C22—C23	121.6 (3)
C6—C5—C4	124.7 (2)	C21—C22—C27	119.1 (3)
C10—C5—C4	118.6 (2)	C23—C22—C27	119.2 (3)
C7—C6—C5	122.1 (2)	C24—C23—C22	121.2 (3)
C7—C6—H6	118.9	C24—C23—H23	119.4
C5—C6—H6	118.9	C22—C23—H23	119.4
C6—C7—C8	120.3 (3)	C23—C24—C25	119.9 (3)
C6—C7—H7	119.9	C23—C24—H24	120.0
C8—C7—H7	119.9	C25—C24—H24	120.0
C9—C8—C7	118.5 (2)	C26—C25—C24	120.9 (3)
C9—C8—C11	119.0 (2)	C26—C25—H25	119.5
C7—C8—C11	122.3 (3)	C24—C25—H25	119.5
C10—C9—C8	121.0 (2)	C25—C26—C27	121.7 (3)
C10—C9—H9	119.5	C25—C26—H26	119.1
C8—C9—H9	119.5	C27—C26—H26	119.1
C9—C10—C5	121.1 (2)	C14—C27—C22	119.8 (3)
C9—C10—H10	119.5	C14—C27—C26	123.3 (3)
C5—C10—H10	119.5	C22—C27—C26	116.9 (3)
C12—C11—N3	107.9 (2)	S3—C28—H28A	109.5
C12—C11—C8	126.8 (3)	S3—C28—H28B	109.5
N3—C11—C8	125.1 (2)	H28A—C28—H28B	109.5
N1—C12—C11	105.5 (2)	S3—C28—H28C	109.5
N1—C12—H12	127.2	H28A—C28—H28C	109.5
C11—C12—H12	127.2	H28B—C28—H28C	109.5

C12—N1—N2—N3	0.3 (3)	C9—C8—C11—C12	−36.6 (4)
C13—N1—N2—N3	−172.9 (3)	C7—C8—C11—C12	139.4 (3)
N1—N2—N3—C11	−0.3 (4)	C9—C8—C11—N3	147.6 (3)
C3—S2—C1—C4	169.8 (2)	C7—C8—C11—N3	−36.3 (4)
C3—S2—C1—S1	−7.97 (19)	N2—N1—C12—C11	−0.2 (3)
C2—S1—C1—C4	−170.3 (3)	C13—N1—C12—C11	172.5 (3)
C2—S1—C1—S2	7.28 (18)	N3—C11—C12—N1	0.0 (3)
C28—S3—C2—C3	155.2 (3)	C8—C11—C12—N1	−176.4 (3)
C28—S3—C2—S1	−30.0 (3)	N2—N1—C13—C14	121.3 (3)
C1—S1—C2—C3	−3.6 (3)	C12—N1—C13—C14	−50.6 (4)
C1—S1—C2—S3	−178.7 (2)	N1—C13—C14—C27	−79.6 (3)
S3—C2—C3—S2	173.3 (2)	N1—C13—C14—C15	97.9 (3)
S1—C2—C3—S2	−1.5 (4)	C27—C14—C15—C16	178.1 (3)
S3—C2—C3—S4	−7.9 (5)	C13—C14—C15—C16	0.7 (4)
S1—C2—C3—S4	177.2 (2)	C27—C14—C15—C20	−1.7 (4)
S3—C2—C3—S4A	29.4 (5)	C13—C14—C15—C20	−179.1 (2)
S1—C2—C3—S4A	−145.4 (4)	C14—C15—C16—C17	177.0 (3)
C1—S2—C3—C2	5.9 (3)	C20—C15—C16—C17	−3.2 (4)
C1—S2—C3—S4	−173.1 (2)	C15—C16—C17—C18	−0.2 (6)
C1—S2—C3—S4A	147.4 (4)	C16—C17—C18—C19	2.9 (6)
C29—S4—C3—C2	91.4 (4)	C17—C18—C19—C20	−2.0 (6)
C29—S4—C3—S2	−89.8 (3)	C18—C19—C20—C21	−179.8 (3)
C29—S4—C3—S4A	14.2 (5)	C18—C19—C20—C15	−1.5 (5)
C29A—S4A—C3—C2	−130.5 (9)	C14—C15—C20—C21	2.1 (4)
C29A—S4A—C3—S2	86.7 (9)	C16—C15—C20—C21	−177.7 (3)
C29A—S4A—C3—S4	−8.5 (8)	C14—C15—C20—C19	−176.2 (3)
S2—C1—C4—C5	−176.68 (19)	C16—C15—C20—C19	4.0 (4)
S1—C1—C4—C5	0.7 (4)	C19—C20—C21—C22	176.5 (3)
S2—C1—C4—C4ⁱ	−2.8 (3)	C15—C20—C21—C22	−1.8 (4)
S1—C1—C4—C4ⁱ	174.61 (18)	C20—C21—C22—C23	−178.4 (3)
C1—C4—C5—C6	−27.2 (4)	C20—C21—C22—C27	1.0 (4)
C4ⁱ—C4—C5—C6	159.0 (2)	C21—C22—C23—C24	178.2 (3)
C1—C4—C5—C10	150.5 (3)	C27—C22—C23—C24	−1.2 (4)
C4ⁱ—C4—C5—C10	−23.3 (3)	C22—C23—C24—C25	2.1 (5)
C10—C5—C6—C7	−4.2 (4)	C23—C24—C25—C26	−0.9 (5)
C4—C5—C6—C7	173.5 (2)	C24—C25—C26—C27	−1.1 (5)
C5—C6—C7—C8	−0.8 (4)	C15—C14—C27—C22	1.0 (4)
C6—C7—C8—C9	4.3 (4)	C13—C14—C27—C22	178.4 (2)
C6—C7—C8—C11	−171.8 (2)	C15—C14—C27—C26	−179.4 (2)
C7—C8—C9—C10	−2.6 (4)	C13—C14—C27—C26	−2.0 (4)
C11—C8—C9—C10	173.6 (2)	C21—C22—C27—C14	−0.6 (4)
C8—C9—C10—C5	−2.5 (4)	C23—C22—C27—C14	178.8 (2)
C6—C5—C10—C9	5.8 (4)	C21—C22—C27—C26	179.8 (3)
C4—C5—C10—C9	−172.0 (2)	C23—C22—C27—C26	−0.8 (4)
N2—N3—C11—C12	0.2 (4)	C25—C26—C27—C14	−177.7 (3)
N2—N3—C11—C8	176.6 (3)	C25—C26—C27—C22	1.9 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28C···N2ⁱⁱ	0.98	2.55	3.495 (5)	161
C25—H25···S2ⁱⁱⁱ	0.95	3.00	3.784 (4)	141

Symmetry codes: (ii) −x+1/2, −y+3/2, −z+1; (iii) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₅₈H₄₄N₆S₈
M_r	1081.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	168
a, b, c (Å)	15.906 (4), 14.737 (3), 21.570 (5)
β (°)	98.846 (7)
V (Å³)	4996 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.27 × 0.23 × 0.12

Data collection
Diffractometer	Rigaku AFC8 diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.765, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	24431, 5169, 4127
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.160, 1.06
No. of reflections	5169
No. of parameters	347
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.62

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28C···N2ⁱ	0.9800	2.55	3.495 (5)	161
C25—H25···S2ⁱⁱ	0.9500	3.00	3.784 (4)	141

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x+1/2, −y+3/2, z+1/2.

Acknowledgements

We acknowledge NSERC and the Memorial University of Newfoundland for funding support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Arunan, E., Desiraju, G. R., Klein, R. A., Sadlej, J., Scheiner, S., Alkorta, I., Clary, D. C., Crabtree, R. H., Dannenberg, J. J., Hobza, P., Kjaergaard, H. G., Legon, A. C., Mennucci, B. & Nesbitt, D. J. (2011). Pure Appl. Chem. 83, 1619–1636. Web of Science CrossRef CAS Google Scholar
Bryce, M. R., Moore, A. J., Tanner, B. K., Whitehead, R., Clegg, W., Gerson, F., Lamprecht, A. & Pfenninger, S. (1996). Chem. Mater. 8, 1182–1188. CAS Google Scholar
Desiraju, G. R. (2011). Angew. Chem. Int. Ed. 50, 52–59. Web of Science CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hein, J. E. & Fokin, V. V. (2010). Chem. Soc. Rev. 39, 1302–1315. Web of Science CrossRef CAS PubMed Google Scholar
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Jia, C., Liu, S.-X., Neels, A., Stoeckli-Evans, H. & Decurtins, S. (2005). Synthesis, 13, 2157–2160. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Meldal, M. & Tornøe, C. W. (2008). Chem. Rev. 108, 2952–3015. Web of Science CrossRef PubMed CAS Google Scholar
Mulla, K., Dongare, P., Thompson, D. W. & Zhao, Y. (2012). Org. Biomol. Chem. 10, 2542–2544. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, Y., Chen, G., Mulla, K., Mahmud, I., Liang, S., Dongare, P., Thompson, D. W., Dawe, L. N. & Bouzan, S. (2012). Pure Appl. Chem. 84, 1005–1025. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3298-o3299

doi:10.1107/S1600536812045254

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

1,2-Bis{4-[1-(anthracen-9-ylmeth­yl)-1H-1,2,3-triazol-4-yl]phen­yl}-1,2-bis­­[4,5-bis­­(methyl­sulfan­yl)-1,3-di­thiol-2-yl­­idene]ethane

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,2-Bis{4-[1-(anthracen-9-ylmethyl)-1H-1,2,3-triazol-4-yl]phenyl}-1,2-bis[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]ethane