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The title salt, bis­[2,3-bis­(amino­carbonyl)-8,9-bis­(methyl­sulfanyl)tetra­thia­fulvalenium] di-[mu]-bromido-bis­[bromido­copper(II)], (C10H10N2O2S6)2[Cu2Br4], contains 2,3-bis(aminocarbonyl)-8,9-bis(methylsulfanyl)tetrathiafulvalenium radical cations, [DMT-TTF(CONH2)2]·+, and [Cu2Br4]2- anions. The cations are associated across centres of inversion in a head-to-tail fashion via short face-to-face S...S stacking (TTF moiety). These dimers are further assembled into a one-dimensional chain structure via interdimer double S...S contacts involving the methyl­sulfanyl groups. The one-dimensional chains give rise to a two-dimensional structure through inter­molecular double N-H...O hydrogen bonds involving the amide group. The [Cu2Br4]2- anions, which straddle centres of inversion, are located between the cation layers. Electron paramagnetic resonance measurements show a radical signal, indicating that the two TTF·+ radicals are not completely coupled in the dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107042035/sq3096sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107042035/sq3096Isup2.hkl
Contains datablock I

CCDC reference: 669156

Comment top

Although tetrathiafulvalene (TTF) and its derivatives have been intensively investigated for several decades, these unique functional molecules continue to attract great attention, especially for their inter- or intramolecular interactions. These weak interactions play a very important role in supramolecular assembly and the modification of the physical properties of these materials (Williams et al., 1985; Hudhomme et al. 2001; Rovira & Novoa, 1999). We have previously reported some radical salts with S···S and C···C intermolecular contacts (Lu et al., 2006, 2007). In this report, a new salt of (2,3-bis(amide)-8,9-bis(methylsulfanyl)-tetrathiafulvalene), [DMT-TTF(CONH2)2]2Cu2Br4, (I), is described. The intra- and intermolecular interactions in its structure are detailed herein.

Radical or charge-transfer salts are usually prepared by two techniques. The majority are obtained by electrocrystallization and the rest through chemical oxidation. The chemical oxidation method typically utilizes halogens and a number of transition metal salts in their higher oxidation state (e.g. CuII, FeIII and HgII). In this preparation, the TTF moiety of the precursor DMT-TTF(CONH2)2 was oxidized by one electron during the reaction by a CuII salt which is reduced to CuI, forming a dinuclear anion.

The title compound, (I), is a radical cation salt with [Cu2Br4]2− anions and coupled [DMT-TTF(CONH2)2].+ cations (Fig. 1). Both cation and anion are essentially planar. The two CuI ions are bridged by two Br ions across a centre of inversion, to form a dinuclear anion with the Cu atom in a triangular coordination environment. As expected, the terminal Cu—Br2 bonds are a little shorter than the bridging Cu—Br1 bonds, which themselves differ slightly (Table 1). To the best of our knowledge, this structure of the [Cu2Br4]2− anion has not been reported in TTF salts to date; most such salts are further coordinated and the CuI centre takes a tetrahedral geometry (Moustarder et al., 2002; Kanehama et al., 2003).

In the TTF units of (I), the central CC bond distance [C3C4 = 1.376 (4) Å] is longer than that found in neutral TTF compounds and is in agreement with that of TTF.+ radicals (Lu et al., 2007). The IR stretching band of the central CC bond at 1347 cm−1 shows a red shift relative to 1403 cm−1 for the neutral compound. It is known that the central CC stretching of TTF undergoes a large frequency shift on oxidation (>50–100 cm−1) (Siedle et al., 1980; Matsubayashi et al., 1988). There is an intramolecular N—H···O hydrogen bond between the two ortho-amide groups (Fig. 1 and Table 2).

Compound (I) crystallizes in the triclinic system, with one (C10H10N2O4S6)2Cu2Br4 formula in the unit cell (the asymmetric unit consists of one TTF.+ cation and half of a [Cu2Br4]2− anion). The cations are paired across centers of inversion to form a dimeric structure in a head-to-tail mode via short S···S stacking (Figure 1). The S···S distances of 3.339 (1) Å (S3···S4ii), 3.419 (1) Å (S1···S6ii) and 3.515 (1) Å (S2···S5ii) (symmetry operation ii:-x, 1 − y, 2 − z) indicate very effective stacking within the TTF dimer. The dimers further assemble into a one-dimensional step structure along the [0 1 0] direction through inter-dimer S···S contacts between –SCH3 units (S5···S6iii, 3.348 (1) Å, iii:-x, 2 − y, 2 − z) (Figure 2). These one-dimensional chains then give rise to a two-dimensional structure in the (011) plane through inter-chain double N—H···O hydrogen bonds (Fig. 3). Fig. 4 shows the cooperation of the hydrogen bonds and the S···S contacts. The [Cu2Br4]2− anions are located between the (011) planes and linked to two cations through Br···H—N hydrogen bonds (Table 2).

It is noteworthy that no short intermolecular C···C contact involving the central CC bond was found within the TTF dimer. The electron paramagnetic resonance spectrum shows a radical signal (g = 2.003), which means that the two TTF.+ radicals are not completely coupled in the dimer. This result is in accordance with the conclusion we presumed in our earlier paper (Lu et al., 2007), namely that the short intermolecular C···C contact in the centre of the TTF moiety is the most important indicator of the coupling of the two radicals.

Experimental top

The precursor, 2,3-bis(methylcarboxylate)-8,9-bis(methylsulfanyl) tetrathiafulvalene, C12H12O4S6, was synthesized using a reported coupling method (Baudron et al., 2003). The neutral 2,3-bis(amide)-8,9-bis(methylsulfanyl)tetrathiafulvalene, DMT-TTF(CONH2)2, was obtained by reaction of the bis(methylcarboxylate) derivative with ammonia (Hudhomme et al., 2001; McCullough et al., 1999).

[DMT-TTF(CONH2)2]2Cu2Br4, (I), was obtained by careful addition of a solution of CuBr2 (44.6 mg, 0.2 mmol) in acetonitrile (6 ml) to a solution of 2,3-bis(amide)-8,9-bis(methylsulfanyl)tetrathiafulvalene (7.6 mg, 0.02 mmol) in tetrahydrofuran (5 ml) in a straight tube (7 mm in diameter). The glass tube was sealed and the two solutions were kept unmixed. After 3 d, black crystals of (I) suitable for X-ray crystallographic analysis were obtained at the interface of the two phases. These were washed with acetonitrile and dried in vacuo (yield 15.90 mg, 66%). IR (KBr disc, ν, cm−1): 3419 (NH), 3157 (NH), 1665 (CO), 1347 (CC). Analysis, calculated for C20H20N4O4S12Cu2Br4: C 19.80, H 1.65, N, 4.62%; found: C 19.63, H 1.51, N 4.50%.

Refinement top

H atoms were positioned with idealized geometry and refined with fixed isotropic displacement parameters [N—H = 0.88 Å and C—H 0.98 Å; Uiso(H) = 1.2Ueq(N) or 1.5Ueq(C)].

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalStructure (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Intermolecular S···S interactions in the TTF dimer and intramolecular N—H···O hydrogen bonds are shown as dashed lines. H atoms have been omitted for clarity. Unlabelled atoms are related to labelled atoms by the symmetry operator (−x, −y, −z). [Please check added symmetry code]
[Figure 2] Fig. 2. Diagram showing how the molecular couples assemble into a one-dimensional step structure via intermolecular double S···S contacts (dashed lines).
[Figure 3] Fig. 3. The packing of the TTF cations, showing the two-dimensional structure. Intermolecular contacts are shown as dotted lines. The [Cu2Br4]2− anions are located between these layers, which stack along the a axis.
[Figure 4] Fig. 4. The cooperation of the double N—H···O hydrogen bonds and double S···S contacts in the molecular assembly of (I).
bis[2,3-bis(aminocarbonyl)-8,9-bis(methylsulfanyl)tetrathiafulvalenium] di-µ-bromido-bis[bromidocopper(II)] top
Crystal data top
(C10H10N2O2S6)2[Cu2Br4]Z = 1
Mr = 1211.84F(000) = 590
Triclinic, P1Dx = 2.248 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3326 (9) ÅCell parameters from 3221 reflections
b = 10.0980 (9) Åθ = 3.2–25.3°
c = 10.3272 (9) ŵ = 6.39 mm1
α = 75.343 (7)°T = 173 K
β = 72.571 (6)°Block, black
γ = 81.242 (7)°0.30 × 0.16 × 0.15 mm
V = 895.25 (14) Å3
Data collection top
Rigaku Mercury
diffractometer
3252 independent reflections
Radiation source: fine-focus sealed tube2819 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 7.31 pixels mm-1θmax = 25.3°, θmin = 3.3°
ω scansh = 1011
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1012
Tmin = 0.218, Tmax = 0.383l = 1212
8740 measured reflections
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0374P)2 + 0.3125P]
where P = (Fo2 + 2Fc2)/3
3252 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.61 e Å3
Crystal data top
(C10H10N2O2S6)2[Cu2Br4]γ = 81.242 (7)°
Mr = 1211.84V = 895.25 (14) Å3
Triclinic, P1Z = 1
a = 9.3326 (9) ÅMo Kα radiation
b = 10.0980 (9) ŵ = 6.39 mm1
c = 10.3272 (9) ÅT = 173 K
α = 75.343 (7)°0.30 × 0.16 × 0.15 mm
β = 72.571 (6)°
Data collection top
Rigaku Mercury
diffractometer
3252 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
2819 reflections with I > 2σ(I)
Tmin = 0.218, Tmax = 0.383Rint = 0.025
8740 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.070H-atom parameters constrained
S = 1.05Δρmax = 0.70 e Å3
3252 reflectionsΔρmin = 0.61 e Å3
211 parameters
Special details top

Experimental. Elemental analyses of C, H and N were performed using an EA 1110 elemental analyzer. IR spectra were recorded as KBr discs on a Nicolet Magna 550 F T—IR spectrometer. ESR spectra were recorded on an EMX-10/12 spectrometer at 110 K.

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*/Ueq
Br10.64254 (4)0.67476 (4)0.51131 (4)0.03293 (12)
Br20.66287 (4)0.36038 (4)0.70806 (4)0.03273 (12)
Cu10.56406 (5)0.45958 (5)0.57833 (5)0.03348 (13)
S10.30665 (8)0.26603 (8)0.81083 (9)0.02176 (19)
S20.07505 (9)0.36260 (8)0.66596 (9)0.0249 (2)
S30.24747 (9)0.53601 (8)0.92818 (9)0.02259 (19)
S40.00101 (9)0.63548 (8)0.79918 (8)0.02099 (18)
S50.20648 (9)0.78932 (9)1.04565 (10)0.0285 (2)
S60.05540 (9)0.90009 (8)0.90017 (9)0.02288 (19)
O10.4595 (3)0.0273 (2)0.8186 (3)0.0317 (6)
O20.1692 (3)0.0157 (2)0.5433 (3)0.0317 (6)
N10.3954 (3)0.0661 (3)0.6687 (3)0.0316 (7)
H1A0.46030.13840.67830.038*
H1B0.33800.05790.61280.038*
N20.0338 (3)0.1669 (3)0.5616 (3)0.0286 (7)
H2A0.07620.12380.52040.034*
H2B0.08040.24140.58970.034*
C10.2746 (3)0.1559 (3)0.7189 (3)0.0207 (7)
C20.1646 (3)0.1979 (3)0.6551 (3)0.0197 (7)
C30.1686 (3)0.3918 (3)0.7753 (3)0.0193 (7)
C40.1413 (3)0.5084 (3)0.8277 (3)0.0203 (7)
C50.1595 (3)0.6949 (3)0.9476 (3)0.0202 (7)
C60.0435 (3)0.7424 (3)0.8868 (3)0.0186 (7)
C70.3939 (4)0.7215 (4)1.0510 (4)0.0325 (9)
H7A0.39130.62811.10890.049*
H7B0.43630.77991.09050.049*
H7C0.45660.71950.95640.049*
C80.2029 (4)0.9012 (4)0.8201 (4)0.0294 (8)
H8A0.15900.90640.72020.044*
H8B0.27520.98100.83410.044*
H8C0.25460.81690.86250.044*
C90.3841 (4)0.0295 (3)0.7378 (3)0.0240 (7)
C100.1009 (4)0.1195 (3)0.5813 (3)0.0236 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0274 (2)0.0315 (2)0.0413 (2)0.00280 (15)0.01117 (16)0.01141 (17)
Br20.0319 (2)0.0373 (2)0.0385 (2)0.00222 (16)0.01675 (16)0.01716 (17)
Cu10.0343 (3)0.0400 (3)0.0322 (3)0.0110 (2)0.0101 (2)0.0126 (2)
S10.0176 (4)0.0261 (4)0.0266 (5)0.0013 (3)0.0105 (3)0.0111 (4)
S20.0304 (5)0.0228 (4)0.0292 (5)0.0051 (3)0.0180 (4)0.0117 (4)
S30.0176 (4)0.0246 (4)0.0317 (5)0.0014 (3)0.0109 (3)0.0138 (4)
S40.0213 (4)0.0221 (4)0.0243 (4)0.0002 (3)0.0111 (3)0.0085 (3)
S50.0206 (4)0.0316 (5)0.0444 (6)0.0024 (4)0.0150 (4)0.0231 (4)
S60.0210 (4)0.0205 (4)0.0322 (5)0.0011 (3)0.0117 (4)0.0112 (4)
O10.0323 (13)0.0300 (13)0.0415 (15)0.0060 (11)0.0236 (12)0.0123 (12)
O20.0365 (14)0.0297 (13)0.0413 (15)0.0098 (11)0.0229 (12)0.0225 (12)
N10.0317 (16)0.0332 (16)0.0369 (18)0.0106 (13)0.0191 (14)0.0161 (15)
N20.0312 (16)0.0263 (15)0.0388 (18)0.0031 (13)0.0205 (14)0.0160 (14)
C10.0190 (16)0.0227 (16)0.0209 (17)0.0036 (13)0.0022 (13)0.0085 (14)
C20.0221 (16)0.0191 (15)0.0180 (16)0.0004 (13)0.0057 (13)0.0052 (13)
C30.0166 (15)0.0215 (16)0.0208 (17)0.0003 (13)0.0066 (13)0.0058 (14)
C40.0176 (16)0.0224 (16)0.0230 (17)0.0007 (13)0.0074 (13)0.0074 (14)
C50.0177 (16)0.0192 (16)0.0251 (18)0.0028 (13)0.0046 (13)0.0082 (14)
C60.0175 (16)0.0202 (16)0.0194 (17)0.0044 (13)0.0041 (13)0.0063 (14)
C70.0210 (17)0.038 (2)0.047 (2)0.0040 (15)0.0198 (17)0.0154 (18)
C80.0284 (19)0.0284 (18)0.038 (2)0.0009 (15)0.0187 (16)0.0095 (16)
C90.0194 (17)0.0254 (17)0.0247 (18)0.0016 (14)0.0057 (14)0.0037 (15)
C100.0280 (18)0.0285 (18)0.0190 (17)0.0025 (15)0.0122 (14)0.0065 (15)
Geometric parameters (Å, º) top
Br1—Cu12.3895 (6)O2—C101.231 (4)
Br1—Cu1i2.4601 (6)N1—C91.313 (4)
Br2—Cu12.3129 (6)N1—H1A0.8800
Cu1—Br1i2.4601 (6)N1—H1B0.8800
Cu1—Cu1i2.6149 (8)N2—C101.331 (4)
S1—C31.720 (3)N2—H2A0.8800
S1—C11.741 (3)N2—H2B0.8800
S2—C31.721 (3)C1—C21.342 (5)
S2—C21.758 (3)C1—C91.519 (4)
S3—C51.718 (3)C2—C101.510 (4)
S3—C41.727 (3)C3—C41.376 (4)
S4—C41.724 (3)C5—C61.376 (4)
S4—C61.727 (3)C7—H7A0.9800
S5—C51.734 (3)C7—H7B0.9800
S5—C71.790 (3)C7—H7C0.9800
S6—C61.730 (3)C8—H8A0.9800
S6—C81.803 (3)C8—H8B0.9800
O1—C91.237 (4)C8—H8C0.9800
Cu1—Br1—Cu1i65.24 (2)S1—C3—S2114.95 (17)
Cu1—Br2—H1A89.6C3—C4—S4123.2 (2)
Br2—Cu1—Br1128.38 (2)C3—C4—S3121.2 (2)
Br2—Cu1—Br1i116.82 (2)S4—C4—S3115.59 (18)
Br1—Cu1—Br1i114.760 (19)C6—C5—S3116.8 (2)
Br2—Cu1—Cu1i172.65 (3)C6—C5—S5120.7 (2)
Br1—Cu1—Cu1i58.684 (19)S3—C5—S5122.45 (19)
Br1i—Cu1—Cu1i56.08 (2)C5—C6—S4116.5 (2)
C3—S1—C196.18 (15)C5—C6—S6121.4 (2)
C3—S2—C295.73 (15)S4—C6—S6122.17 (18)
C5—S3—C495.59 (15)S5—C7—H7A109.5
C4—S4—C695.48 (15)S5—C7—H7B109.5
C5—S5—C7104.04 (16)H7A—C7—H7B109.5
C6—S6—C8102.56 (15)S5—C7—H7C109.5
C9—N1—H1A120.0H7A—C7—H7C109.5
C9—N1—H1B120.0H7B—C7—H7C109.5
H1A—N1—H1B120.0S6—C8—H8A109.5
C10—N2—H2A120.0S6—C8—H8B109.5
C10—N2—H2B120.0H8A—C8—H8B109.5
H2A—N2—H2B120.0S6—C8—H8C109.5
C2—C1—C9136.6 (3)H8A—C8—H8C109.5
C2—C1—S1116.7 (2)H8B—C8—H8C109.5
C9—C1—S1106.7 (2)O1—C9—N1124.8 (3)
C1—C2—C10128.6 (3)O1—C9—C1115.0 (3)
C1—C2—S2116.2 (2)N1—C9—C1120.2 (3)
C10—C2—S2115.1 (2)O2—C10—N2121.7 (3)
C4—C3—S1121.3 (2)O2—C10—C2121.6 (3)
C4—C3—S2123.7 (2)N2—C10—C2116.7 (3)
H1A—Br2—Cu1—Br1178.7C5—S3—C4—C3177.6 (3)
H1A—Br2—Cu1—Br1i1.3C5—S3—C4—S42.5 (2)
H1A—Br2—Cu1—Cu1i15.5C4—S3—C5—C61.4 (3)
Cu1i—Br1—Cu1—Br2177.52 (4)C4—S3—C5—S5178.4 (2)
Cu1i—Br1—Cu1—Br1i0.0C7—S5—C5—C6160.9 (3)
C3—S1—C1—C20.2 (3)C7—S5—C5—S322.2 (3)
C3—S1—C1—C9178.5 (2)S3—C5—C6—S40.2 (4)
C9—C1—C2—C105.1 (6)S5—C5—C6—S4176.83 (17)
S1—C1—C2—C10173.0 (3)S3—C5—C6—S6179.39 (17)
C9—C1—C2—S2178.7 (3)S5—C5—C6—S62.4 (4)
S1—C1—C2—S23.2 (4)C4—S4—C6—C51.7 (3)
C3—S2—C2—C14.8 (3)C4—S4—C6—S6179.1 (2)
C3—S2—C2—C10171.9 (2)C8—S6—C6—C5174.1 (3)
C1—S1—C3—C4178.8 (3)C8—S6—C6—S45.0 (2)
C1—S1—C3—S23.5 (2)C2—C1—C9—O1173.0 (4)
C2—S2—C3—C4177.5 (3)S1—C1—C9—O15.2 (4)
C2—S2—C3—S14.8 (2)C2—C1—C9—N18.3 (6)
S1—C3—C4—S4178.22 (18)S1—C1—C9—N1173.5 (3)
S2—C3—C4—S44.3 (4)C1—C2—C10—O217.7 (5)
S1—C3—C4—S31.6 (4)S2—C2—C10—O2166.0 (3)
S2—C3—C4—S3175.88 (18)C1—C2—C10—N2161.2 (3)
C6—S4—C4—C3177.5 (3)S2—C2—C10—N215.0 (4)
C6—S4—C4—S32.6 (2)
Symmetry code: (i) x+1, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Br20.882.723.601 (3)180
N1—H1B···O20.881.902.717 (4)154
N2—H2A···O2ii0.882.092.951 (4)167
N2—H2B···S20.882.442.906 (3)114
N2—H2B···Br1iii0.882.883.317 (3)112
C7—H7A···Br2iv0.982.903.870 (4)172
C7—H7B···S1v0.982.813.529 (3)131
C7—H7C···Br2vi0.982.923.880 (4)165
C8—H8B···O1iii0.982.493.216 (4)130
C8—H8C···Br2iii0.982.993.648 (3)126
Symmetry codes: (ii) x, y, z+1; (iii) x1, y+1, z; (iv) x+1, y, z+2; (v) x+1, y+1, z+2; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formula(C10H10N2O2S6)2[Cu2Br4]
Mr1211.84
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.3326 (9), 10.0980 (9), 10.3272 (9)
α, β, γ (°)75.343 (7), 72.571 (6), 81.242 (7)
V3)895.25 (14)
Z1
Radiation typeMo Kα
µ (mm1)6.39
Crystal size (mm)0.30 × 0.16 × 0.15
Data collection
DiffractometerRigaku Mercury
diffractometer
Absorption correctionMulti-scan
(Jacobson, 1998)
Tmin, Tmax0.218, 0.383
No. of measured, independent and
observed [I > 2σ(I)] reflections
8740, 3252, 2819
Rint0.025
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.070, 1.05
No. of reflections3252
No. of parameters211
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.70, 0.61

Computer programs: CrystalClear (Rigaku, 2001), CrystalStructure (Rigaku, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-32 (Farrugia, 1997), publCIF (Westrip, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Br20.882.723.601 (3)179.5
N1—H1B···O20.881.902.717 (4)154.2
N2—H2A···O2i0.882.092.951 (4)167.4
N2—H2B···S20.882.442.906 (3)113.9
N2—H2B···Br1ii0.882.883.317 (3)112.3
C7—H7A···Br2iii0.982.903.870 (4)171.7
C7—H7B···S1iv0.982.813.529 (3)130.8
C7—H7C···Br2v0.982.923.880 (4)165.1
C8—H8B···O1ii0.982.493.216 (4)130.4
C8—H8C···Br2ii0.982.993.648 (3)125.6
Symmetry codes: (i) x, y, z+1; (ii) x1, y+1, z; (iii) x+1, y, z+2; (iv) x+1, y+1, z+2; (v) x, y+1, z.
 

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