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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3138
https://doi.org/10.1107/S160053681104339X

Di­ethyl 2,5-bis­­[(2,3-di­hydro­thieno[3,4-b][1,4]dioxin-5-yl)methyl­­idene­amino]­thio­phene-3,4-di­carboxyl­ate acetone monosolvate

Stéphane Dufresne,a Andréanne Bolduca and W. G. Skenea*

aDepartment of Chemistry, University of Montreal, CP 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7
*Correspondence e-mail: w.skene@umontreal.ca

(Received 30 August 2011; accepted 19 October 2011; online 2 November 2011)

The unique 3,4-ethyl­ene­dioxy­thio­phene (EDOT) unit of the title compound, C24H22N2O8S3·C3H6O, is twisted by 1.9 (3)° relative to the central thio­phene ring. The three heterocyclic units are anti­periplanar. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds connect the heterocycles. π–π interactions occur between the central thiophene and the imine bond of the molecule [distance between the ring centroid of the ring and the azomethine bond = 3.413 (3) Å.

Related literature

For general background, see: Dufresne et al. (2007[Dufresne, S., Bourgeaux, M. & Skene, W. G. (2007). J. Mater. Chem. 17, 1-13.]). For related structures, see: Dufresne et al. (2006[Dufresne, S., Bourgeaux, M. & Skene, W. G. (2006). Acta Cryst. E62, o5602-o5604.]). For π–π inter­actions, see: Janiak (2000[Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]).

[Scheme 1]

Experimental

Crystal data

  • C24H22N2O8S3·C3H6O

  • Mr = 620.69

  • Monoclinic, C 2/c

  • a = 13.288 (3) Å

  • b = 23.541 (5) Å

  • c = 9.0627 (18) Å

  • β = 98.27 (3)°

  • V = 2805.5 (10) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 2.91 mm−1

  • T = 150 K

  • 0.25 × 0.10 × 0.04 mm
Data collection

  • Bruker SMART 6000 diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.530, Tmax = 0.892

  • 16861 measured reflections

  • 2718 independent reflections

  • 2215 reflections with I > 2σ(I)

  • Rint = 0.060
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.101

  • S = 1.05

  • 2718 reflections

  • 189 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯O1i 0.95 2.58 3.514 (3) 168 (2)
Symmetry code: (i) -x, -y, -z-1.

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 2004[Bruker (2004). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: UdMX (Marris, 2004[Marris, T. (2004). UdMX. Université de Montréal, Montréal, Québec, Canada.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104339X/mw2024sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104339X/mw2024Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104339X/mw2024Isup3.cml

checkCIF report


Comment top

Compound (I) was prepared during our on-going research on conjugated azomethines. The title compound is one of a limited number of reported crystal structures of 3,4-ethylenedioxythiophene (EDOT) azomethine derivatives. The structure was confirmed by the X-ray crystal structure and, as shown in Fig. 1, the azomethine bond adopts the thermodynamically stable E isomer. Both the title compound and the molecule of acetone solvent crystallized within the lattice have crystallographically imposed C2 symmetry.

A major point of interest is the azomethine bond. The bond lengths for C6—C7, N1—C7 and N1—C8 are 1.430 (2), 1.287 (2) and 1.378 (2) Å, respectively. The bond distances are consistent with those of similar compounds consisting uniquely of thiophenes with two azomethine bonds (Dufresne et al., 2006). The analogous bond lengths for the all-thiophene counterpart are: 1.441 (4), 1.272 (3) and 1.388 (3) Å.

It was found that the azomethine bond is nearly coplanar the terminal EDOT and the central thiophene. Thus the angle between the planes defined by S1, C1, C2, C5, C6 and S2, C8, C8B, C9, C9B is 1.9 (3)°. This is smaller than that in the all-thiophene analogue where the terminal thiophenes are twisted by 9.04 (4)° and 25.07 (6)° from the central thiophene.

The three-dimensional network of (I) involves multiple interactions that are in part responsible for the molecular organization of the crystal lattice. As can be seen in Fig. 2, there is a pair-wise supramolecular arrangement involving a C—H···O interaction between C1H1 in one EDOT and O1 in the EDOT at -x, -y, -1-z (Table 1). This donor–acceptor arrangement leads to a linear and planar organization between different molecules within the lattice. There are also π–π interactions between the thiophene ring containing S1, C1, C2, C5, C6 and the centroid of the azomethine bond (C7, N1) in the molecule at 1-x, -y, -z. The distance between the centroids of the ring and the azomethine bond was found to be 3.413 (3) Å. This separation is in the middle of the range associated with π–π stacking interactions (Janiak, 2000). The organization of the molecules of (I) within in the lattice is aligned in a ladder-type orientation.

Related literature top

For general background, see: Dufresne et al. (2007). For related structures, see: Dufresne et al. (2006). For π–π interactions, see: Janiak (2000).

Experimental top

2,3-dihydrothieno[3,4-b][1,4]dioxine-5-carbaldehyde (112.3 mg, 0.66 mmol) and diethyl 2,5-diaminothiophene-3,4-dicarboxylate (77.3 mg, 0.3 mmol) were dissolved in toluene (20 ml) followed by the addition of DABCO (268 mg, 2.4 mmol) and titanium tetrachloride (1 M, 0.6 ml). The reaction mixture was refluxed for 3 h, concentrated, and then re-dissolved in acetone. The solution was filtered and the solvent was evaporated. The crude product was loaded onto a silica column and eluted with hexanes/ethyl acetate, up to (70%/30% v/v). The product was a red solid (169 mg, 70%). Single crystals of (I) were obtained by slow evaporation of an acetone solution of (I).

Refinement top

H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and included in the refinement in the riding-model approximation, with Uiso(H) = 1.2Ueq(C).

Structure description top

Compound (I) was prepared during our on-going research on conjugated azomethines. The title compound is one of a limited number of reported crystal structures of 3,4-ethylenedioxythiophene (EDOT) azomethine derivatives. The structure was confirmed by the X-ray crystal structure and, as shown in Fig. 1, the azomethine bond adopts the thermodynamically stable E isomer. Both the title compound and the molecule of acetone solvent crystallized within the lattice have crystallographically imposed C2 symmetry.

A major point of interest is the azomethine bond. The bond lengths for C6—C7, N1—C7 and N1—C8 are 1.430 (2), 1.287 (2) and 1.378 (2) Å, respectively. The bond distances are consistent with those of similar compounds consisting uniquely of thiophenes with two azomethine bonds (Dufresne et al., 2006). The analogous bond lengths for the all-thiophene counterpart are: 1.441 (4), 1.272 (3) and 1.388 (3) Å.

It was found that the azomethine bond is nearly coplanar the terminal EDOT and the central thiophene. Thus the angle between the planes defined by S1, C1, C2, C5, C6 and S2, C8, C8B, C9, C9B is 1.9 (3)°. This is smaller than that in the all-thiophene analogue where the terminal thiophenes are twisted by 9.04 (4)° and 25.07 (6)° from the central thiophene.

The three-dimensional network of (I) involves multiple interactions that are in part responsible for the molecular organization of the crystal lattice. As can be seen in Fig. 2, there is a pair-wise supramolecular arrangement involving a C—H···O interaction between C1H1 in one EDOT and O1 in the EDOT at -x, -y, -1-z (Table 1). This donor–acceptor arrangement leads to a linear and planar organization between different molecules within the lattice. There are also π–π interactions between the thiophene ring containing S1, C1, C2, C5, C6 and the centroid of the azomethine bond (C7, N1) in the molecule at 1-x, -y, -z. The distance between the centroids of the ring and the azomethine bond was found to be 3.413 (3) Å. This separation is in the middle of the range associated with π–π stacking interactions (Janiak, 2000). The organization of the molecules of (I) within in the lattice is aligned in a ladder-type orientation.

For general background, see: Dufresne et al. (2007). For related structures, see: Dufresne et al. (2006). For π–π interactions, see: Janiak (2000).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2004); 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: UdMX (Marris, 2004).

Figures top
[Figure 1] Fig. 1. ORTEP representation of (I) with the numbering scheme adopted (SHELXTL; Sheldrick, 2008). Ellipsoids drawn at 30% probability level. Solvent molecules and hydrogens were omitted for clarity.
[Figure 2] Fig. 2. Supramolecular structure showing the intermolecular H-bonding giving the structural arrangement. Dashed lines indicate hydrogen bonds. Hydrogens were omitted for clarity. [Symmetry codes: (i) -x, -y, -1-z].
Diethyl 2,5-bis[(2,3-dihydrothieno[3,4-b][1,4]dioxin-5- yl)methylideneamino]thiophene-3,4-dicarboxylate acetone monosolvate top
Crystal data top
C24H22N2O8S3·C3H6OF(000) = 1296
Mr = 620.69Dx = 1.470 Mg m−3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 13.288 (3) Åθ = 15.0–30.0°
b = 23.541 (5) ŵ = 2.91 mm−1
c = 9.0627 (18) ÅT = 150 K
β = 98.27 (3)°Needle, red
V = 2805.5 (10) Å30.25 × 0.10 × 0.04 mm
Z = 4
Data collection top
Bruker SMART 6000
diffractometer		2718 independent reflections
Radiation source: Rotating anode2215 reflections with I > 2σ(I)
Montel 200 optics monochromatorRint = 0.060
Detector resolution: 5.5 pixels mm-1θmax = 72.0°, θmin = 3.8°
ω scansh = −16→16
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −28→28
Tmin = 0.530, Tmax = 0.892l = −8→10
16861 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0584P)2 + 0.6834P]
where P = (Fo2 + 2Fc2)/3
2718 reflections(Δ/σ)max < 0.001
189 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C24H22N2O8S3·C3H6OV = 2805.5 (10) Å3
Mr = 620.69Z = 4
Monoclinic, C2/cCu Kα radiation
a = 13.288 (3) ŵ = 2.91 mm−1
b = 23.541 (5) ÅT = 150 K
c = 9.0627 (18) Å0.25 × 0.10 × 0.04 mm
β = 98.27 (3)°
Data collection top
Bruker SMART 6000
diffractometer		2718 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2215 reflections with I > 2σ(I)
Tmin = 0.530, Tmax = 0.892Rint = 0.060
16861 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.05Δρmax = 0.25 e Å−3
2718 reflectionsΔρmin = −0.37 e Å−3
189 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
xyzUiso*/Ueq
S20.50000.01366 (3)0.25000.02556 (17)
S10.18156 (4)0.05553 (2)−0.22135 (6)0.02949 (15)
O10.06743 (10)−0.08612 (6)−0.39079 (15)0.0293 (3)
O40.39123 (10)0.20642 (5)0.24719 (14)0.0283 (3)
O20.23045 (10)−0.10493 (6)−0.14440 (15)0.0302 (3)
C80.42699 (13)0.06598 (8)0.1453 (2)0.0231 (4)
N10.34663 (11)0.05550 (7)0.03454 (18)0.0257 (4)
C60.24046 (13)−0.00282 (8)−0.1303 (2)0.0245 (4)
O30.37191 (11)0.18269 (6)0.00449 (15)0.0357 (4)
C50.19872 (14)−0.05222 (8)−0.1925 (2)0.0242 (4)
C40.15966 (15)−0.14861 (8)−0.2055 (2)0.0314 (5)
H4A0.1004−0.1489−0.15060.038*
H4B0.1931−0.1862−0.19230.038*
C90.45815 (13)0.11955 (8)0.1910 (2)0.0226 (4)
C100.40336 (13)0.17185 (8)0.1330 (2)0.0250 (4)
C70.32136 (13)0.00486 (8)−0.0096 (2)0.0252 (4)
H70.3560−0.02710.03740.030*
C110.34758 (16)0.26181 (8)0.2084 (2)0.0349 (5)
H11A0.27620.25800.16010.042*
H11B0.38680.28170.13910.042*
C10.10182 (15)0.01334 (8)−0.3404 (2)0.0292 (4)
H10.05140.0275−0.41650.035*
C20.11942 (14)−0.04248 (8)−0.3127 (2)0.0249 (4)
C30.12391 (15)−0.13842 (8)−0.3688 (2)0.0311 (5)
H3A0.1834−0.1367−0.42310.037*
H3B0.0803−0.1704−0.41000.037*
C120.3528 (2)0.29398 (10)0.3526 (3)0.0482 (6)
H12A0.31620.27290.42150.072*
H12B0.32150.33150.33340.072*
H12C0.42400.29860.39700.072*
O910.00000.74454 (10)0.75000.0691 (8)
C920.00000.69316 (13)0.75000.0366 (7)
C91−0.07780 (18)0.65932 (12)0.6544 (3)0.0545 (7)
H91A−0.11990.63880.71720.082*
H91B−0.04410.63200.59610.082*
H91C−0.12090.68470.58670.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0214 (3)0.0267 (4)0.0269 (4)0.000−0.0023 (2)0.000
S10.0292 (3)0.0272 (3)0.0296 (3)−0.00025 (19)−0.0042 (2)−0.00046 (18)
O10.0256 (7)0.0320 (8)0.0279 (8)−0.0038 (6)−0.0040 (6)−0.0044 (6)
O40.0320 (7)0.0265 (7)0.0253 (8)0.0075 (6)0.0003 (5)0.0018 (5)
O20.0288 (7)0.0267 (7)0.0321 (8)−0.0010 (6)−0.0062 (6)0.0006 (6)
C80.0180 (9)0.0294 (10)0.0213 (10)0.0014 (7)0.0009 (7)−0.0003 (7)
N10.0190 (8)0.0323 (9)0.0241 (9)0.0003 (6)−0.0024 (6)−0.0027 (6)
C60.0201 (9)0.0284 (10)0.0241 (10)−0.0005 (7)0.0003 (7)−0.0010 (7)
O30.0384 (8)0.0421 (9)0.0236 (8)0.0084 (6)−0.0057 (6)0.0033 (6)
C50.0210 (9)0.0283 (10)0.0229 (10)0.0000 (7)0.0017 (7)0.0011 (7)
C40.0288 (10)0.0268 (10)0.0374 (12)−0.0023 (8)0.0012 (8)−0.0024 (8)
C90.0173 (9)0.0292 (10)0.0202 (10)−0.0008 (7)−0.0009 (7)−0.0011 (7)
C100.0190 (9)0.0304 (10)0.0245 (10)−0.0014 (7)−0.0008 (7)0.0003 (8)
C70.0209 (9)0.0306 (10)0.0235 (11)0.0002 (8)0.0009 (7)0.0000 (8)
C110.0380 (11)0.0282 (11)0.0386 (13)0.0087 (9)0.0054 (9)0.0086 (9)
C10.0263 (10)0.0340 (11)0.0250 (11)−0.0011 (8)−0.0040 (8)−0.0003 (8)
C20.0193 (9)0.0332 (10)0.0212 (10)−0.0027 (7)−0.0002 (7)−0.0034 (8)
C30.0296 (10)0.0292 (11)0.0337 (12)−0.0035 (8)0.0019 (8)−0.0068 (8)
C120.0624 (16)0.0313 (12)0.0499 (16)0.0116 (11)0.0047 (12)−0.0037 (10)
O910.102 (2)0.0302 (13)0.083 (2)0.0000.0377 (18)0.000
C920.0398 (17)0.0344 (16)0.0376 (19)0.0000.0125 (13)0.000
C910.0423 (14)0.0741 (19)0.0455 (16)−0.0120 (13)0.0003 (11)0.0037 (13)
Geometric parameters (Å, º) top
S2—C8i1.7591 (19)C9—C9i1.427 (3)
S2—C81.7591 (19)C9—C101.487 (2)
S1—C11.716 (2)C7—H70.9500
S1—C61.7305 (19)C11—C121.504 (3)
O1—C21.376 (2)C11—H11A0.9900
O1—C31.441 (2)C11—H11B0.9900
O4—C101.345 (2)C1—C21.352 (3)
O4—C111.450 (2)C1—H10.9500
O2—C51.362 (2)C3—H3A0.9900
O2—C41.449 (2)C3—H3B0.9900
C8—C91.373 (2)C12—H12A0.9800
C8—N11.378 (2)C12—H12B0.9800
N1—C71.287 (2)C12—H12C0.9800
C6—C51.374 (2)O91—C921.209 (4)
C6—C71.430 (2)C92—C911.482 (3)
O3—C101.206 (2)C92—C91ii1.482 (3)
C5—C21.421 (2)C91—H91A0.9800
C4—C31.508 (3)C91—H91B0.9800
C4—H4A0.9900C91—H91C0.9800
C4—H4B0.9900
C8i—S2—C891.11 (12)C12—C11—H11A110.5
C1—S1—C692.09 (9)O4—C11—H11B110.5
C2—O1—C3110.73 (14)C12—C11—H11B110.5
C10—O4—C11116.47 (15)H11A—C11—H11B108.7
C5—O2—C4111.74 (14)C2—C1—S1111.79 (15)
C9—C8—N1123.57 (16)C2—C1—H1124.1
C9—C8—S2111.18 (14)S1—C1—H1124.1
N1—C8—S2125.22 (14)C1—C2—O1124.73 (17)
C7—N1—C8122.18 (17)C1—C2—C5112.87 (17)
C5—C6—C7129.44 (18)O1—C2—C5122.40 (17)
C5—C6—S1110.36 (14)O1—C3—C4110.85 (16)
C7—C6—S1120.20 (14)O1—C3—H3A109.5
O2—C5—C6123.48 (17)C4—C3—H3A109.5
O2—C5—C2123.63 (17)O1—C3—H3B109.5
C6—C5—C2112.89 (17)C4—C3—H3B109.5
O2—C4—C3110.95 (16)H3A—C3—H3B108.1
O2—C4—H4A109.4C11—C12—H12A109.5
C3—C4—H4A109.4C11—C12—H12B109.5
O2—C4—H4B109.4H12A—C12—H12B109.5
C3—C4—H4B109.4C11—C12—H12C109.5
H4A—C4—H4B108.0H12A—C12—H12C109.5
C8—C9—C9i113.26 (10)H12B—C12—H12C109.5
C8—C9—C10122.85 (16)O91—C92—C91122.52 (15)
C9i—C9—C10123.63 (10)O91—C92—C91ii122.52 (15)
O3—C10—O4123.50 (18)C91—C92—C91ii115.0 (3)
O3—C10—C9126.89 (18)C92—C91—H91A109.5
O4—C10—C9109.60 (15)C92—C91—H91B109.5
N1—C7—C6119.26 (18)H91A—C91—H91B109.5
N1—C7—H7120.4C92—C91—H91C109.5
C6—C7—H7120.4H91A—C91—H91C109.5
O4—C11—C12105.98 (17)H91B—C91—H91C109.5
O4—C11—H11A110.5
C8i—S2—C8—C9−0.34 (9)C8—C9—C10—O3−45.5 (3)
C8i—S2—C8—N1−178.4 (2)C9i—C9—C10—O3140.6 (2)
C9—C8—N1—C7177.54 (18)C8—C9—C10—O4133.27 (18)
S2—C8—N1—C7−4.6 (3)C9i—C9—C10—O4−40.6 (3)
C1—S1—C6—C50.26 (16)C8—N1—C7—C6−176.81 (17)
C1—S1—C6—C7179.57 (16)C5—C6—C7—N1−177.75 (19)
C4—O2—C5—C6166.96 (18)S1—C6—C7—N13.1 (3)
C4—O2—C5—C2−13.4 (3)C10—O4—C11—C12−173.97 (17)
C7—C6—C5—O20.3 (3)C6—S1—C1—C2−0.26 (16)
S1—C6—C5—O2179.49 (14)S1—C1—C2—O1−179.73 (14)
C7—C6—C5—C2−179.43 (19)S1—C1—C2—C50.2 (2)
S1—C6—C5—C2−0.2 (2)C3—O1—C2—C1161.14 (19)
C5—O2—C4—C343.3 (2)C3—O1—C2—C5−18.8 (2)
N1—C8—C9—C9i179.0 (2)O2—C5—C2—C1−179.69 (17)
S2—C8—C9—C9i0.9 (3)C6—C5—C2—C10.0 (2)
N1—C8—C9—C104.5 (3)O2—C5—C2—O10.2 (3)
S2—C8—C9—C10−173.54 (14)C6—C5—C2—O1179.92 (16)
C11—O4—C10—O3−6.8 (3)C2—O1—C3—C448.8 (2)
C11—O4—C10—C9174.33 (15)O2—C4—C3—O1−63.9 (2)
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1iii0.952.583.514 (3)168 (2)
Symmetry code: (iii) −x, −y, −z−1.

Experimental details

Crystal data
Chemical formulaC24H22N2O8S3·C3H6O
Mr620.69
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)13.288 (3), 23.541 (5), 9.0627 (18)
β (°) 98.27 (3)
V (Å3)2805.5 (10)
Z4
Radiation typeCu Kα
µ (mm−1)2.91
Crystal size (mm)0.25 × 0.10 × 0.04
Data collection
DiffractometerBruker SMART 6000
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.530, 0.892
No. of measured, independent and
observed [I > 2σ(I)] reflections		16861, 2718, 2215
Rint0.060
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.101, 1.05
No. of reflections2718
No. of parameters189
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.25, −0.37

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), UdMX (Marris, 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.952.583.514 (3)168 (2)
Symmetry code: (i) −x, −y, −z−1.
 

Acknowledgements

The authors acknowledge financial support from the Natural Sciences and Engineering Research Council Canada (NSERC), the Centre for Self-Assembled Chemical Structures, and the Canada Foundation for Innovation. Both SD and AB thank both NSERC and the Université de Montréal for graduate scholarships.

References

First citationBruker (2003). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2004). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDufresne, S., Bourgeaux, M. & Skene, W. G. (2006). Acta Cryst. E62, o5602–o5604.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationDufresne, S., Bourgeaux, M. & Skene, W. G. (2007). J. Mater. Chem. 17, 1–13.  Web of Science CSD CrossRef Google Scholar
 First citationJaniak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896.  Web of Science CrossRef Google Scholar
 First citationMarris, T. (2004). UdMX. Université de Montréal, Montréal, Québec, Canada.  Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3138
https://doi.org/10.1107/S160053681104339X
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