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In the title compound, (C10H9NOS6)K[Hg(SCN)4] or (EDT–TTF–CONHMe)K[Hg(SCN)4)], fully oxidized organic (EDT–TTF–CONHMe) radical cations form quasi-one-dimensional stacks running along the monoclinic 21 axis and alternating along the crystallographic [101] direction with inorganic anion stacks made from mixed K+–[Hg(SCN)4]2− ribbons. For each anion, three essentially collinear SCN ligands inter­act with the K+ ions via short N...K contacts, while the terminal N atom of the fourth SCN group is engaged in a number of hydrogen-bond contacts with the –CH, –NH and –CH2 hydrogen-bond donors of the amide function. Radical cations are dimerized along the stacks and the crystal conductivity is activated.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107006154/av3066sup1.cif
Contains datablocks global, I, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107006154/av3066Isup2.hkl
Contains datablock I

CCDC reference: 641791

Comment top

3',4'-Ethylenedithio-3-methylamido-tetrathiafulvalene (EDT–TTF–CONHMe; Heuzé et al., 1999) is one of a series of π-donor molecules whose hydrogen-bond donor/acceptor group acts in the solid state as a structure-directing functionality, eventually enhanced upon redox activation (Fourmigué & Batail, 2004), as illustrated by several recent examples (Heuzé et al., 2000, 2003; Baudron et al., 2003). The anion, [Hg(SCN)4]2-, was selected to be used in the title compound because of its versatile conformation in addition to a noted ability to form metallic and superconducting radical cation salts with a variety of organic donors.

As exemplified in Fig. 1, radical cation stacks and chains of anionic motifs are segregated and run along the monoclinic 21 axis. The labeled molecules with displacement ellipsoids are shown in Figs. 2 (organic donor) and 3(b) (anion), respectively. There is one independent radical cation located in a general position. The central C1C2 bond length [1.391 (5) Å] of the TTF fragment is the most sensitive to the degree of charge transfer, or net π-donor oxidation state, and is characteristic of a fully oxidized (1+) donor molecule. A zigzag mode of intermolecular overlap with two different patterns of overlap is observed, indicating that the stack is dimerized (Fig. 2). The intradimer overlap A qualifies a strong intradimer interaction with short S···S, S···C and C···C van der Waals contacts, presented in Table 1 and Fig. 3(a), while only one S3···S3 contact for interdimer interaction B is observed. The intra- and inter-dimer interplanar separations within the stack, calculated using the central six atoms of the TTF fragment, are 3.355 (8) and 3.460 (8) Å, respectively.

The complex anion, K+[Hg(SCN)4]2-, is located in a general position near the twofold screw axis 21. The Hg atom adopts a tetrahedral coordination by S atoms, yet each of the SCN ligand adjusts to the crystal environment by rotating around the Hg—S bonds. Note that the conformation of the anion revealed in (I) has not been reported previously. Analysis of structures collected in the Cambridge Structural Database (Bruno et al., 2002; Allen, 2002) indicates that, in the previously reported structures, at most two SCN vectors of the [Hg(SCN)4]2- anion appear to be near collinear instead of three in the present compound. These three ligands interact with the K+ ion via short N···K contacts of 2.780 (4)–3.108 (4) Å, stabilizing the anion ribbon as shown in Fig. 3(b). The fourth SCN ligand protrudes out towards the donor molecules, its terminal N2A atom being involved in a number of hydrogen contacts with the amide groups (Fig. 3a and Table 2). The recurrent tweezer-like hydrogen-bonded seven-membered ring motif (Heuzé et al., 2000; Fourmigué & Batail, 2004) acting upon the combined effect of activated –NH and –Csp2H hydrogen-bond donors, is again identified here. In addition, the radical cation stacks are connected to adjacent anion ribbons by short O···K [2.606 (3) Å] and S···S contacts along [101]. The coordination polyhedron around the K+ cation is a distorted octahedron composed of one O and five N atoms; this differs from the eight- (4 N + 4S) and seven-coordination (4 N + 3S) of K in α- and δ-(BEDT-TTF)2K[Hg(SCN)4], respectively (Oshima et al., 1989; Kazheva et al., 2002). The crystals of (I) are semiconducting, as expected for a dimerized stack.

Related literature top

For related literature, see: Allen (2002); Baudron et al. (2003); Bruno et al. (2002); Fourmigué & Batail (2004); Heuzé et al. (1999, 2000, 2003); Kazheva et al. (2002); Oshima et al. (1989); Sheldrick (1997).

Experimental top

Single crystals of (I) were obtained by electrooxidation, at constant current (I = 2 µA) and 293 K, of the above donor in 1,1,2-trichloroethane solution containing 10%(v/v) of dried ethanol. Plate-like crystals grew on the anode after three weeks.

Refinement top

The final refinement was carried out in space group P21/n, chosen on the basis of the systematic absences and successful refinement of the structure. The positions of the methyl and ethylene H atoms were calculated as riding, in accordance with HFIX 137 and HFIX 23 instructions of SHELXL97 (Sheldrick, 1997), with Uiso(H) values of 1.5 and 1.2 times Ueq(C), respectively. The H atoms of –Csp2H and –NH groups were located in difference electron density syntheses and constrained by AFIX 43 [Uiso(H) = 1.2Ueq(C,N)]. The terminal ethylene group of the radical cation is disordered over two positions in a \sim3:1 ratio and C—C distances were restrained to be equal.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2 and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The crystal structure of (I).
[Figure 2] Fig. 2. Intra- (A) and inter-dimer (B) patterns of overlap between the radical cations along the stack. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. (a) Donor–donor (dashed lines) and donor–anion (dotted lines) interactions. (b) The anion ribbon stabilized by N···K contacts. [Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (i) -x + 2, -y + 1, -z + 1; (ii) -x + 2, -y + 2, -z + 1; (iv) x + 1, y + 1, z; (v) -x + 3/2, y + 1/2, -z + 1/2; (vi) x, y + 1, z.]
potassium 3',4'-ethylenedithio-3-methylamidotetrathiafulvalene(+) tetraisothiocyanatomercury(II) top
Crystal data top
K(C10H9NOS6)[Hg(SCN)4]F(000) = 1580
Mr = 823.55Dx = 2.065 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7058 reflections
a = 13.7129 (17) Åθ = 3.0–25.1°
b = 7.9403 (9) ŵ = 6.78 mm1
c = 24.862 (3) ÅT = 294 K
β = 101.879 (5)°Small, black
V = 2649.2 (6) Å30.15 × 0.06 × 0.02 mm
Z = 4
Data collection top
Bruker X8Apex CCD detector
diffractometer
6827 independent reflections
Radiation source: fine-focus sealed tube4594 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω and ϕ scansθmax = 29.5°, θmin = 3.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1518
Tmin = 0.430, Tmax = 0.876k = 1010
25746 measured reflectionsl = 3434
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0176P)2 + 0.5772P]
where P = (Fo2 + 2Fc2)/3
6827 reflections(Δ/σ)max = 0.002
309 parametersΔρmax = 0.88 e Å3
1 restraintΔρmin = 0.61 e Å3
Crystal data top
K(C10H9NOS6)[Hg(SCN)4]V = 2649.2 (6) Å3
Mr = 823.55Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.7129 (17) ŵ = 6.78 mm1
b = 7.9403 (9) ÅT = 294 K
c = 24.862 (3) Å0.15 × 0.06 × 0.02 mm
β = 101.879 (5)°
Data collection top
Bruker X8Apex CCD detector
diffractometer
6827 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4594 reflections with I > 2σ(I)
Tmin = 0.430, Tmax = 0.876Rint = 0.040
25746 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.069H-atom parameters constrained
S = 1.02Δρmax = 0.88 e Å3
6827 reflectionsΔρmin = 0.61 e Å3
309 parameters
Special details top

Experimental. The DC resistance measurements were performed on single crystals by the two-probe method with the current flow applied along a stack direction in the 300 – 4.2 K temperature interval. Four annealed platinum wires (10 µm in diameter) were attached to a crystal surface by a graphite paste. The applied current was 10–20 µA.

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
xyzUiso*/UeqOcc. (<1)
K10.75749 (6)0.75738 (11)0.24987 (3)0.0543 (2)
Hg10.545783 (10)0.17603 (2)0.405668 (6)0.05455 (7)
S1A0.57404 (9)0.49464 (14)0.40134 (4)0.0665 (3)
S2A0.42967 (9)0.18028 (17)0.47338 (5)0.0775 (4)
S3A0.70128 (7)0.00148 (14)0.43133 (4)0.0630 (3)
S4A0.44076 (8)0.06819 (16)0.31431 (4)0.0679 (3)
C1A0.6468 (3)0.5093 (5)0.35541 (15)0.0552 (10)
C2A0.3259 (3)0.1450 (4)0.42753 (18)0.0544 (10)
C3A0.7625 (3)0.0745 (5)0.38504 (16)0.0597 (10)
C4A0.5364 (3)0.0068 (5)0.28683 (15)0.0554 (10)
N1A0.6971 (3)0.5234 (4)0.32416 (15)0.0749 (11)
N2A0.2527 (3)0.1223 (5)0.39675 (18)0.0778 (11)
N3A0.8090 (3)0.1246 (6)0.35470 (16)0.0953 (14)
N4A0.6007 (3)0.0348 (5)0.26654 (15)0.0793 (11)
S10.95388 (7)0.63311 (12)0.59003 (3)0.0468 (2)
S20.79938 (7)0.54608 (11)0.49483 (3)0.0465 (2)
S31.07862 (7)0.81842 (10)0.50766 (4)0.0445 (2)
S40.91880 (6)0.72987 (12)0.41446 (4)0.0453 (2)
S50.85699 (9)0.47352 (14)0.67181 (4)0.0673 (3)
S60.67353 (9)0.35747 (15)0.55617 (5)0.0702 (3)
C10.9125 (3)0.6423 (4)0.51974 (14)0.0421 (8)
C20.9645 (3)0.7223 (4)0.48453 (14)0.0420 (8)
C30.8539 (3)0.5168 (4)0.60246 (14)0.0447 (8)
C40.7817 (3)0.4746 (4)0.55869 (13)0.0434 (8)
C51.0896 (3)0.8895 (4)0.44392 (14)0.0448 (8)
H51.14490.95160.43930.054*
C61.0157 (3)0.8524 (4)0.40067 (14)0.0435 (8)
C70.7252 (6)0.4346 (11)0.6668 (3)0.078 (3)0.772 (13)
H7A0.71430.40220.70270.094*0.772 (13)
H7B0.68900.53850.65630.094*0.772 (13)
C80.6836 (10)0.3000 (11)0.6260 (4)0.076 (3)0.772 (13)
H8A0.61800.26890.63160.091*0.772 (13)
H8B0.72580.20110.63350.091*0.772 (13)
C7A0.7563 (13)0.315 (3)0.6708 (7)0.052 (6)0.228 (13)
H7C0.77720.20550.66000.063*0.228 (13)
H7D0.74080.30470.70710.063*0.228 (13)
C8A0.667 (2)0.375 (5)0.6301 (12)0.062 (9)0.228 (13)
H8C0.65530.49270.63790.075*0.228 (13)
H8D0.60900.31240.63580.075*0.228 (13)
C91.0028 (3)0.8939 (5)0.34079 (15)0.0497 (9)
C101.0619 (4)1.0440 (6)0.26857 (16)0.0840 (14)
H10A1.06960.94490.24770.126*
H10B1.11371.12300.26600.126*
H10C0.99811.09420.25420.126*
N11.0682 (2)0.9981 (4)0.32603 (12)0.0569 (8)
H11.11531.03950.35080.068*
O10.9321 (2)0.8306 (3)0.30909 (11)0.0678 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K10.0548 (5)0.0585 (5)0.0513 (5)0.0006 (4)0.0147 (4)0.0047 (4)
Hg10.03656 (10)0.08054 (13)0.04928 (10)0.00362 (7)0.01514 (7)0.00187 (7)
S1A0.0664 (7)0.0698 (7)0.0700 (7)0.0063 (6)0.0291 (6)0.0114 (5)
S2A0.0497 (7)0.1372 (11)0.0519 (6)0.0130 (6)0.0251 (5)0.0146 (6)
S3A0.0426 (6)0.0915 (8)0.0578 (6)0.0094 (5)0.0168 (5)0.0222 (5)
S4A0.0462 (6)0.1066 (9)0.0504 (6)0.0049 (6)0.0085 (5)0.0158 (6)
C1A0.059 (3)0.052 (2)0.052 (2)0.005 (2)0.007 (2)0.0028 (18)
C2A0.051 (3)0.046 (2)0.075 (3)0.0051 (18)0.034 (2)0.0074 (18)
C3A0.042 (2)0.086 (3)0.050 (2)0.019 (2)0.0059 (19)0.016 (2)
C4A0.055 (3)0.066 (3)0.046 (2)0.006 (2)0.0105 (19)0.0053 (18)
N1A0.097 (3)0.066 (2)0.072 (2)0.010 (2)0.042 (2)0.0002 (18)
N2A0.043 (2)0.077 (2)0.116 (3)0.0107 (19)0.023 (2)0.008 (2)
N3A0.070 (3)0.146 (4)0.079 (3)0.034 (3)0.036 (2)0.053 (3)
N4A0.075 (3)0.090 (3)0.077 (2)0.009 (2)0.027 (2)0.008 (2)
S10.0436 (6)0.0534 (5)0.0430 (5)0.0010 (4)0.0075 (4)0.0065 (4)
S20.0362 (5)0.0568 (5)0.0457 (5)0.0021 (4)0.0062 (4)0.0056 (4)
S30.0367 (5)0.0480 (5)0.0486 (5)0.0027 (4)0.0082 (4)0.0053 (4)
S40.0367 (5)0.0522 (5)0.0464 (5)0.0045 (4)0.0070 (4)0.0014 (4)
S50.0777 (8)0.0828 (7)0.0443 (5)0.0019 (6)0.0196 (5)0.0041 (5)
S60.0541 (7)0.0852 (8)0.0730 (7)0.0195 (6)0.0167 (6)0.0107 (6)
C10.039 (2)0.0409 (19)0.0463 (19)0.0025 (15)0.0086 (16)0.0041 (15)
C20.038 (2)0.0411 (19)0.047 (2)0.0042 (15)0.0085 (16)0.0027 (15)
C30.046 (2)0.0435 (19)0.047 (2)0.0057 (16)0.0151 (17)0.0003 (15)
C40.040 (2)0.0449 (19)0.047 (2)0.0073 (16)0.0128 (16)0.0056 (15)
C50.039 (2)0.0446 (19)0.054 (2)0.0037 (16)0.0171 (17)0.0070 (16)
C60.0367 (19)0.042 (2)0.053 (2)0.0011 (15)0.0124 (17)0.0045 (15)
C70.073 (5)0.106 (6)0.066 (4)0.019 (5)0.040 (4)0.018 (4)
C80.074 (7)0.070 (6)0.094 (6)0.004 (4)0.040 (5)0.025 (5)
C7A0.052 (12)0.059 (14)0.051 (11)0.018 (9)0.023 (9)0.024 (9)
C8A0.031 (12)0.10 (3)0.059 (16)0.002 (16)0.010 (11)0.017 (18)
C90.047 (2)0.056 (2)0.049 (2)0.0033 (19)0.0165 (19)0.0046 (18)
C100.096 (4)0.104 (4)0.058 (3)0.027 (3)0.033 (3)0.004 (2)
N10.056 (2)0.068 (2)0.0496 (17)0.0116 (17)0.0191 (15)0.0051 (15)
O10.064 (2)0.087 (2)0.0508 (16)0.0227 (15)0.0079 (15)0.0072 (14)
Geometric parameters (Å, º) top
Hg1—S3A2.5259 (10)S6—C81.773 (11)
Hg1—S2A2.5444 (11)S6—C8A1.86 (3)
Hg1—S1A2.5650 (12)C1—C21.391 (5)
Hg1—S4A2.5729 (10)C3—C41.354 (5)
S1A—C1A1.668 (4)C5—C61.349 (5)
S2A—C2A1.654 (5)C5—H50.9300
S3A—C3A1.671 (4)C6—C91.499 (5)
S4A—C4A1.672 (4)C7—C81.502 (9)
C1A—N1A1.146 (5)C7—H7A0.9700
C2A—N2A1.144 (5)C7—H7B0.9700
C3A—N3A1.154 (5)C8—H8A0.9700
C4A—N4A1.150 (5)C8—H8B0.9700
S1—C11.724 (3)C7A—C8A1.504 (11)
S1—C31.733 (4)C7A—H7C0.9700
S2—C11.726 (4)C7A—H7D0.9700
S2—C41.749 (3)C8A—H8C0.9700
S3—C51.718 (4)C8A—H8D0.9700
S3—C21.730 (4)C9—O11.224 (4)
S4—C21.727 (3)C9—N11.327 (4)
S4—C61.737 (4)C10—N11.459 (5)
S5—C31.750 (3)C10—H10A0.9600
S5—C71.812 (7)C10—H10B0.9600
S5—C7A1.87 (2)C10—H10C0.9600
S6—C41.741 (4)N1—H10.8600
S1···S4i3.384 (1)C1···C1i3.577 (7)
S2···S3i3.350 (1)C4···C5i3.394 (5)
S3···S3ii3.574 (2)C1···C2i3.363 (5)
S3···C4i3.620 (3)C3···C6i3.442 (5)
S5···C9i3.543 (4)C3···C5i3.564 (5)
S3A—Hg1—S2A116.81 (3)C9—C6—S4112.3 (3)
S3A—Hg1—S1A115.72 (4)C8—C7—S5113.7 (7)
S2A—Hg1—S1A97.77 (4)C8—C7—H7A108.8
S3A—Hg1—S4A109.11 (4)S5—C7—H7A108.8
S2A—Hg1—S4A106.00 (4)C8—C7—H7B108.8
S1A—Hg1—S4A110.68 (4)S5—C7—H7B108.8
C1A—S1A—Hg1102.38 (14)H7A—C7—H7B107.7
C2A—S2A—Hg196.24 (14)C7—C8—S6114.8 (7)
C3A—S3A—Hg198.17 (13)C7—C8—H8A108.6
C4A—S4A—Hg196.54 (13)S6—C8—H8A108.6
N1A—C1A—S1A178.4 (4)C7—C8—H8B108.6
N2A—C2A—S2A178.2 (4)S6—C8—H8B108.6
N3A—C3A—S3A176.7 (4)H8A—C8—H8B107.5
N4A—C4A—S4A178.2 (4)C8A—C7A—S5107 (2)
C1—S1—C395.52 (17)C8A—C7A—H7C110.3
C1—S2—C495.75 (16)S5—C7A—H7C110.3
C5—S3—C294.79 (17)C8A—C7A—H7D110.3
C2—S4—C694.89 (17)S5—C7A—H7D110.3
C3—S5—C798.3 (3)H7C—C7A—H7D108.6
C3—S5—C7A104.6 (5)C7A—C8A—S6116 (2)
C4—S6—C8102.0 (4)C7A—C8A—H8C108.3
C4—S6—C8A98.0 (11)S6—C8A—H8C108.3
C2—C1—S1123.6 (3)C7A—C8A—H8D108.3
C2—C1—S2121.0 (3)S6—C8A—H8D108.3
S1—C1—S2115.4 (2)H8C—C8A—H8D107.4
C1—C2—S4121.6 (3)O1—C9—N1124.7 (4)
C1—C2—S3122.5 (3)O1—C9—C6117.7 (3)
S4—C2—S3115.8 (2)N1—C9—C6117.6 (3)
C4—C3—S1117.6 (3)N1—C10—H10A109.5
C4—C3—S5127.5 (3)N1—C10—H10B109.5
S1—C3—S5114.9 (2)H10A—C10—H10B109.5
C3—C4—S6129.6 (3)N1—C10—H10C109.5
C3—C4—S2115.8 (3)H10A—C10—H10C109.5
S6—C4—S2114.64 (19)H10B—C10—H10C109.5
C6—C5—S3118.0 (3)C9—N1—C10121.3 (3)
C6—C5—H5121.0C9—N1—H1119.4
S3—C5—H5121.0C10—N1—H1119.4
C5—C6—C9131.2 (3)C9—O1—K1165.8 (3)
C5—C6—S4116.4 (3)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7C···N1i0.972.633.45 (2)142
C8—H8B···N2Aiii0.972.713.539 (9)144
N1—H1···N2Aiv0.862.102.938 (5)165
C5—H5···N2Aiv0.932.413.298 (5)160
Symmetry codes: (i) x+2, y+1, z+1; (iii) x+1, y, z+1; (iv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaK(C10H9NOS6)[Hg(SCN)4]
Mr823.55
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)13.7129 (17), 7.9403 (9), 24.862 (3)
β (°) 101.879 (5)
V3)2649.2 (6)
Z4
Radiation typeMo Kα
µ (mm1)6.78
Crystal size (mm)0.15 × 0.06 × 0.02
Data collection
DiffractometerBruker X8Apex CCD detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.430, 0.876
No. of measured, independent and
observed [I > 2σ(I)] reflections
25746, 6827, 4594
Rint0.040
(sin θ/λ)max1)0.692
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.069, 1.02
No. of reflections6827
No. of parameters309
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.88, 0.61

Computer programs: APEX2 (Bruker, 2005), APEX2 and WinGX (Farrugia, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected interatomic distances (Å) top
S1···S4i3.384 (1)C1···C1i3.577 (7)
S2···S3i3.350 (1)C4···C5i3.394 (5)
S3···S3ii3.574 (2)C1···C2i3.363 (5)
S3···C4i3.620 (3)C3···C6i3.442 (5)
S5···C9i3.543 (4)C3···C5i3.564 (5)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7C···N1i0.972.633.45 (2)142
C8—H8B···N2Aiii0.972.713.539 (9)144
N1—H1···N2Aiv0.862.102.938 (5)165
C5—H5···N2Aiv0.932.413.298 (5)160
Symmetry codes: (i) x+2, y+1, z+1; (iii) x+1, y, z+1; (iv) x+1, y+1, z.
 

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