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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o912-o913

5-(Naphthalen-1-yl)isophthalic acid–di­methyl sulfoxide–water (2/1/2)

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: Edwin.Weber@chemie.tu-freiberg.de

(Received 17 April 2013; accepted 6 May 2013; online 18 May 2013)

The asymmetric unit of the title compound, 2C18H12O4·C2H6OS·2H2O, consists of four crystallographically independent mol­ecules of 5-(naphthalen-1-yl)isophthalic acid, two dimethyl sulfoxide and four water mol­ecules. The dihedral angles formed by the the planes of the aromatic fragments of the organic mol­ecules range from 57.4 (1) to 59.1 (1)°. In the crystal, multiple O—H⋯O hydrogen bonds link the water mol­ecules with the carbonyl and sulfoxide groups, giving rise to double ribbons along the b-axis direction.

Related literature

For preparative methods used for the synthesis of the title compound, see: Broutin & Colobert (2005[Broutin, P.-E. & Colobert, F. (2005). Eur. J. Org. Chem. pp. 1113-1128.]); Mazik & König (2006[Mazik, M. & König, A. (2006). J. Org. Chem. 71, 7854-7857.]); Miyaura et al. (1981[Miyaura, N., Yanagi, T. & Suzuki, A. (1981). Synth. Commun. 11, 513-519.]). For the structure of isophthalic acid, see: Derissen (1974[Derissen, J. L. (1974). Acta Cryst. B30, 2764-2765.]). For hydrogen-bonding patterns, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]); Burrows (2004[Burrows, A. D. (2004). Struct. Bond. 108, 55-96.]). For ππ stacking inter­actions, see: James (2004[James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.]). For C—H⋯O inter­actions, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. New York: Oxford University Press Inc.]). For organic crystal engineering aspects, see: Tiekink et al. (2010[Tiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Chichester: Wiley.]).

[Scheme 1]

Experimental

Crystal data
  • 2C18H12O4·C2H6OS·2H2O

  • Mr = 698.72

  • Triclinic, P 1

  • a = 6.6842 (4) Å

  • b = 9.6173 (6) Å

  • c = 25.4682 (15) Å

  • α = 95.780 (3)°

  • β = 95.669 (3)°

  • γ = 90.028 (3)°

  • V = 1620.82 (17) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 93 K

  • 0.18 × 0.17 × 0.09 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 39842 measured reflections

  • 15284 independent reflections

  • 12600 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.100

  • S = 1.04

  • 15284 reflections

  • 945 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 7387 Friedel pairs

  • Flack parameter: −0.03 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O1Wi 0.84 1.72 2.559 (2) 175
O1B—H1B⋯O3W 0.84 1.74 2.573 (2) 168
O2A—H2A⋯O4Aii 0.84 1.82 2.583 (2) 151
O2C—H2C⋯O4Cii 0.84 1.81 2.584 (2) 152
O3A—H3A⋯O2Wiii 0.84 1.73 2.565 (3) 174
O3C—H3C⋯O4W 0.84 1.72 2.561 (2) 176
O4—H4⋯O2iii 0.84 1.81 2.591 (2) 154
O4B—H4B⋯O2Biii 0.84 1.81 2.578 (2) 150
O1W—H1W1⋯O1Hiv 0.85 (3) 1.92 (3) 2.716 (3) 155 (3)
O1W—H2W1⋯O3v 0.85 (3) 2.04 (3) 2.858 (2) 162 (3)
O2W—H1W2⋯O1Gvi 0.85 (3) 1.91 (3) 2.742 (3) 168 (3)
O2W—H2W2⋯O1A 0.85 (2) 2.03 (2) 2.879 (2) 174 (3)
O3W—H1W3⋯O1Gvii 0.85 (2) 1.85 (2) 2.680 (3) 165 (3)
O3W—H2W3⋯O3Bii 0.85 (2) 1.98 (2) 2.824 (2) 170 (3)
O4W—H1W4⋯O1Hvii 0.85 (2) 1.84 (2) 2.656 (3) 162 (3)
O4W—H2W4⋯O1Ciii 0.86 (3) 1.96 (3) 2.808 (2) 172 (3)
Symmetry codes: (i) x-1, y+1, z; (ii) x, y+1, z; (iii) x, y-1, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) x-1, y, z+1; (vii) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

In the solid state, isophthalic acid creates an interesting bond stabilized tape structure (Derissen, 1974) with the dimer motif of carboxylic acids (Burrows, 2004) showing particular effectiveness. Substitution of the isophthalic acid with a naphthalene unit that may activate competing π-stacking behaviour in the supramolecular organization (James, 2004) is a challenging question regarding aspects of crystal engineering (Tiekink et al., 2010). This led us to study the crystal structure of a corresponding compound which proved to be a mixed DMSO solvate-hydrate species of 2:1:2 (compound:DMSO:H2O) stoichiometry containing four crystallographically independent compound molecules, two DMSO and four water molecules in the asymmetric part of the unit cell (Fig. 1). Regarding the conformation of the naphthyl substituted isophthalic acid molecule, the dihedral angles formed by the planes of the aromatic moieties range from 57.4 (1) to 59.1 (1)°; the isophthalic acid fragments of the molecules are approximately planar. Due to the distinctive donor/acceptor character of the crystal components, the solid phase structure of the title compound is characterized by a complicated pattern of non-covalent intermolecular bonding. The crystal can be regarded as being constructed of molecular double layers extending parallel to the crystallographic ab plane (Fig. 2). The aromatic parts of the isophthalic acid molecules form the hydrophobic peripheral areas of the double layer structure, whereas the core region is defined by the polar molecule parts and solvent molecules. In this arrangement, the carboxyl groups and water molecules take part in formation of 10-membered cyclic motifs of O—H···O bonds [d(H···O) 1.81–1.82 Å]. Hence, instead of the conventional carboxylic acid dimer of the graph set R22(8) (Bernstein et al., 1995), an expanded dimer following the graph set R33(10) is formed. Furthermore, the second hydrogen of each water molecule is engaged in coordination with DMSO molecules, the O atoms of which act as bifurcated acceptors [d(H···O) 1.85 (2)–1.92 (3) Å]. A large number of relatively strong non- conventional hydrogen bonds of the C—H···O type (Desiraju & Steiner, 1999) [d(H···O) 2.47 (2)–2.55 (3) Å] involving carboxylic and water O atoms complete the network of intermolecular interactions. Within the hydrophobic layer domains, the naphthyl residues of the molecules adopt a herringbone pattern, so that no marked arene based interlayer interactions can be observed. Consequently, only weak van der Waals forces stabilize the crystal packing in direction of the c-axis.

Related literature top

For preparative methods used for the synthesis of the title compound, see: Broutin & Colobert (2005); Mazik & König (2006); Miyaura et al. (1981). For the structure of isophthalic acid, see: Derissen (1974). For hydrogen-bonding patterns, see: Bernstein et al. (1995); Burrows (2004). For ππ stacking interaction, see: James (2004). For C—H···O interactions, see: Desiraju & Steiner (1999). For organic crystal engineering aspects, see: Tiekink et al. (2010).

Experimental top

Preparation of the title compound was achieved by a Suzuki cross coupling reaction (Miyaura et al., 1981) between 2-(naphthalen-1-yl)-1,3,2- dioxaborolane (Broutin & Colobert, 2005) (3.1 g, 9.5 mmol) in the presence of palladium(II) acetate (217 mg, 0.97 mmol) and potassium phosphate (3.0 g, 14.1 mmol) in 70 ml degassed tetrahydrofuran. The resulting mixture was heated to reflux for 6 h, then cooled to room temperature, quenched with water and filtered through celite. The aqueous phase was extracted with dichloromethane and dried over Na2SO4. Evaporation of the solvent and crystallization from ethanol yielded 1.20 g (41%) colourless needles with m.p. 421–422 K of the intermediate diester. This diester and powdered sodium hydroxid (5.0 g, 125 mmol) in methanol-water (50 ml, 1:1, v/v) was refluxed for 4 h. After cooling to room temperature, the mixture was filtered and the filtrate acidified with aqueous hydrochloric acid. The precipitate which has formed was collected by suction filtration, washed with water, dissolved in ethanol-chloroform (1:1) and dried (Na2SO4). Evaporation of the solvent and crystallization from ethanol yielded 1.1 g (40%) of colourless crystals; m.p. > 593 K. IR (KBr) 3063, 2029, 1848, 1706, 1628, 1603, 805, 779, 763. 1H NMR (400 MHz, D6–DMSO) 7.54 - 7.66 (m, 4 H, naphthyl-H), 7.75 (d, 3JHH = 8 Hz, 1 H, naphthyl-H), 8.05 (m, 2 H, naphthyl-H), 8.23 (s, 2 H, isophthalic acid-H), 8.59 (s, 1 H, isophthalic acid-H), 13.33 (br, 2 H, COOH). 13C NMR (100.6 MHz, D6–DMSO) 124.7, 125.7, 126.3, 127.0, 127.4, 128.6, 128.7, 129.0, 130.6, 131.8, 133.5, 134.3, 137.6, 140.8, 166.5 (COOH). MS (EI) m/z: found - 292.1; calc. for C18H12O4 - 292.25. Palladium(II) acetate was purchased from Aldrich. Melting point was measured on a hot stage microscope (Rapido, Dresden). IR, NMR (1H, 13C) and mass (EI–MS) spectra were performed using Nicolet 510 FT–IR, Bruker Avance DPX 400 and Finnigan Mat 8200 instruments, respectively. Crystals of the title compound (DMSO solvate-dihydrate) suitable for X-ray structural analysis were grown by slow evaporating a solution of the material described above.

Refinement top

Aromatic H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å and Uiso = 1.2 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of the title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the a-axis of the crystal packing of the title compound. Hydrogen bond interactions are presented as broken lines. Oxygen atoms are specified as dotted circles, sulfur atoms as shaded circles. Non-relevant hydrogen atoms are omitted.
5-(Naphthalen-1-yl)isophthalic acid–dimethyl sulfoxide–water (2/1/2) top
Crystal data top
2C18H12O4·C2H6OS·2H2OZ = 2
Mr = 698.72F(000) = 732
Triclinic, P1Dx = 1.432 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6842 (4) ÅCell parameters from 8379 reflections
b = 9.6173 (6) Åθ = 2.2–30.6°
c = 25.4682 (15) ŵ = 0.17 mm1
α = 95.780 (3)°T = 93 K
β = 95.669 (3)°Rhombus, colourless
γ = 90.028 (3)°0.18 × 0.17 × 0.09 mm
V = 1620.82 (17) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
12600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 28.1°, θmin = 1.6°
ϕ and ω scansh = 88
39842 measured reflectionsk = 1212
15284 independent reflectionsl = 3333
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2447P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
15284 reflectionsΔρmax = 0.31 e Å3
945 parametersΔρmin = 0.29 e Å3
8 restraintsAbsolute structure: Flack (1983), 7387 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (5)
Crystal data top
2C18H12O4·C2H6OS·2H2Oγ = 90.028 (3)°
Mr = 698.72V = 1620.82 (17) Å3
Triclinic, P1Z = 2
a = 6.6842 (4) ÅMo Kα radiation
b = 9.6173 (6) ŵ = 0.17 mm1
c = 25.4682 (15) ÅT = 93 K
α = 95.780 (3)°0.18 × 0.17 × 0.09 mm
β = 95.669 (3)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
12600 reflections with I > 2σ(I)
39842 measured reflectionsRint = 0.043
15284 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100Δρmax = 0.31 e Å3
S = 1.04Δρmin = 0.29 e Å3
15284 reflectionsAbsolute structure: Flack (1983), 7387 Friedel pairs
945 parametersAbsolute structure parameter: 0.03 (5)
8 restraints
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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. Distances for O—H bonds of the water molecules were restraint of 0.85 (0.01) Angstroms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0444 (3)1.15517 (17)0.93514 (7)0.0183 (4)
H10.05301.23730.94940.027*
O20.0285 (3)1.26400 (17)0.86570 (7)0.0166 (4)
O30.0263 (3)0.63317 (18)0.92376 (7)0.0181 (4)
O40.0604 (3)0.52281 (17)0.84729 (7)0.0173 (4)
H40.04120.45090.86240.026*
C10.1036 (4)0.8755 (2)0.71638 (9)0.0131 (5)
C20.0413 (4)0.9361 (3)0.68468 (10)0.0160 (5)
H20.14760.98470.70040.019*
C30.0365 (4)0.9282 (3)0.62936 (10)0.0179 (5)
H30.13830.97160.60810.021*
C40.1153 (4)0.8578 (3)0.60616 (10)0.0171 (5)
H4A0.11600.85050.56870.021*
C50.2709 (4)0.7959 (2)0.63727 (10)0.0145 (5)
C60.4338 (4)0.7260 (3)0.61436 (10)0.0185 (5)
H60.43540.71720.57690.022*
C70.5862 (4)0.6718 (3)0.64457 (11)0.0217 (6)
H70.69290.62510.62830.026*
C80.5864 (4)0.6849 (3)0.70067 (10)0.0193 (6)
H80.69460.64810.72190.023*
C90.4319 (4)0.7502 (2)0.72416 (10)0.0158 (5)
H90.43460.75870.76170.019*
C100.2673 (4)0.8055 (2)0.69350 (10)0.0130 (5)
C110.0816 (4)0.8818 (2)0.77422 (10)0.0130 (5)
C120.0566 (4)1.0103 (2)0.80377 (9)0.0133 (5)
H120.06211.09430.78720.016*
C130.0237 (4)1.0165 (2)0.85705 (10)0.0120 (5)
C140.0126 (4)0.8948 (2)0.88178 (10)0.0131 (5)
H140.01200.89910.91800.016*
C150.0379 (4)0.7662 (2)0.85273 (10)0.0130 (5)
C160.0729 (4)0.7607 (2)0.79979 (10)0.0136 (5)
H160.09140.67260.78050.016*
C170.0031 (4)1.1579 (3)0.88623 (10)0.0140 (5)
C180.0212 (4)0.6353 (2)0.87888 (10)0.0132 (5)
O1A0.4749 (3)0.58077 (17)0.92172 (7)0.0176 (4)
O2A0.5635 (3)0.65134 (17)0.84584 (7)0.0172 (4)
H2A0.54540.73110.86130.026*
O3A0.4594 (3)0.06583 (18)0.93111 (7)0.0174 (4)
H3A0.45200.00880.94540.026*
O4A0.5295 (3)0.08045 (17)0.86125 (7)0.0169 (4)
C1A0.5968 (4)0.2372 (2)0.71184 (10)0.0142 (5)
C2A0.4496 (4)0.1661 (3)0.67782 (10)0.0166 (5)
H2A10.34290.12190.69200.020*
C3A0.4543 (4)0.1576 (3)0.62245 (10)0.0196 (6)
H3A10.35170.10770.59970.024*
C4A0.6062 (4)0.2212 (3)0.60148 (10)0.0179 (5)
H4A10.60510.21860.56410.022*
C5A0.7651 (4)0.2910 (2)0.63458 (10)0.0153 (5)
C6A0.9278 (4)0.3532 (3)0.61336 (11)0.0211 (6)
H6A0.92870.35030.57600.025*
C7A1.0827 (4)0.4170 (3)0.64568 (11)0.0229 (6)
H7A1.18970.45930.63090.027*
C8A1.0839 (4)0.4202 (3)0.70124 (11)0.0204 (6)
H8A1.19400.46250.72360.024*
C9A0.9294 (4)0.3635 (3)0.72307 (10)0.0168 (5)
H9A0.93300.36720.76060.020*
C10A0.7626 (4)0.2987 (2)0.69084 (10)0.0135 (5)
C11A0.5760 (4)0.2556 (2)0.77016 (10)0.0128 (5)
C12A0.5691 (4)0.3900 (2)0.79653 (10)0.0136 (5)
H12A0.58710.46880.77770.016*
C13A0.5362 (4)0.4105 (2)0.84980 (10)0.0127 (5)
C14A0.5131 (4)0.2966 (2)0.87837 (10)0.0131 (5)
H14A0.49050.31030.91480.016*
C15A0.5235 (4)0.1616 (2)0.85266 (10)0.0128 (5)
C16A0.5526 (4)0.1418 (2)0.79892 (10)0.0140 (5)
H16A0.55660.04960.78170.017*
C17A0.5220 (4)0.5552 (2)0.87681 (10)0.0135 (5)
C18A0.5046 (4)0.0373 (2)0.88190 (10)0.0133 (5)
O1B0.6696 (3)0.72004 (17)0.17136 (7)0.0164 (4)
H1B0.65670.79460.15680.025*
O2B0.7921 (3)0.86549 (17)0.24144 (7)0.0156 (4)
O3B0.6950 (3)0.20477 (17)0.17970 (7)0.0165 (4)
O4B0.8369 (3)0.13335 (17)0.25592 (7)0.0158 (4)
H4B0.79780.05420.24160.024*
C1B0.9745 (4)0.5465 (2)0.39000 (9)0.0132 (5)
C2B0.8542 (4)0.6176 (3)0.42408 (10)0.0164 (5)
H2B0.73670.66190.41000.020*
C3B0.9013 (4)0.6265 (3)0.47989 (11)0.0197 (6)
H3B0.81620.67670.50270.024*
C4B1.0684 (4)0.5630 (3)0.50072 (10)0.0179 (5)
H4B11.09610.56580.53810.022*
C5B1.2014 (4)0.4930 (3)0.46748 (10)0.0163 (5)
C6B1.3807 (4)0.4316 (3)0.48856 (11)0.0197 (6)
H6B1.41070.43500.52590.024*
C7B1.5110 (4)0.3676 (3)0.45596 (11)0.0213 (6)
H7B1.62960.32600.47080.026*
C8B1.4708 (4)0.3630 (3)0.40047 (11)0.0188 (6)
H8B1.56320.31940.37810.023*
C9B1.2992 (4)0.4208 (2)0.37855 (10)0.0156 (5)
H9B1.27460.41790.34110.019*
C10B1.1573 (4)0.4853 (2)0.41101 (9)0.0135 (5)
C11B0.9094 (4)0.5295 (2)0.33200 (9)0.0122 (5)
C12B0.8653 (4)0.6428 (2)0.30312 (10)0.0136 (5)
H12B0.88440.73510.32010.016*
C13B0.7935 (3)0.6225 (2)0.24962 (10)0.0110 (5)
C14B0.7634 (3)0.4884 (2)0.22378 (10)0.0114 (5)
H14B0.71230.47510.18750.014*
C15B0.8097 (4)0.3739 (2)0.25216 (10)0.0118 (5)
C16B0.8828 (4)0.3948 (2)0.30538 (10)0.0130 (5)
H16B0.91540.31610.32420.016*
C17B0.7521 (4)0.7479 (2)0.22060 (9)0.0116 (5)
C18B0.7735 (4)0.2302 (2)0.22478 (10)0.0132 (5)
O1C0.1944 (3)1.14760 (17)0.17794 (7)0.0168 (4)
O2C0.3329 (3)1.25902 (17)0.25475 (7)0.0160 (4)
H2C0.30491.33050.23910.024*
O3C0.1643 (3)0.62594 (17)0.16752 (6)0.0153 (4)
H3C0.13820.54350.15440.023*
O4C0.2889 (3)0.51794 (17)0.23747 (7)0.0157 (4)
C1C0.4779 (4)0.9086 (2)0.38610 (9)0.0123 (5)
C2C0.3567 (4)0.8484 (2)0.41795 (10)0.0158 (5)
H2C10.23770.80040.40250.019*
C3C0.4056 (4)0.8562 (3)0.47333 (10)0.0182 (6)
H3C10.32080.81220.49470.022*
C4C0.5741 (4)0.9268 (3)0.49644 (10)0.0170 (5)
H4C0.60270.93460.53390.020*
C5C0.7072 (4)0.9887 (3)0.46510 (10)0.0147 (5)
C6C0.8870 (4)1.0585 (3)0.48780 (10)0.0176 (5)
H6C0.91791.06720.52520.021*
C7C1.0161 (4)1.1134 (3)0.45698 (11)0.0200 (6)
H7C1.13451.16120.47300.024*
C8C0.9738 (4)1.0991 (3)0.40126 (10)0.0181 (5)
H8C1.06591.13530.37980.022*
C9C0.8014 (4)1.0337 (2)0.37795 (10)0.0150 (5)
H9C0.77521.02510.34040.018*
C10C0.6601 (4)0.9781 (2)0.40893 (9)0.0123 (5)
C11C0.4120 (3)0.9006 (2)0.32818 (9)0.0119 (5)
C12C0.3846 (4)1.0224 (2)0.30269 (9)0.0117 (5)
H12C0.41781.11060.32190.014*
C13C0.3094 (4)1.0156 (2)0.24968 (10)0.0115 (5)
C14C0.2617 (3)0.8869 (2)0.22096 (9)0.0111 (5)
H14C0.20860.88220.18480.013*
C15C0.2925 (3)0.7659 (2)0.24564 (10)0.0109 (5)
C16C0.3660 (4)0.7733 (2)0.29906 (9)0.0121 (5)
H16C0.38470.68960.31570.015*
C17C0.2729 (4)1.1463 (2)0.22324 (10)0.0127 (5)
C18C0.2487 (4)0.6250 (2)0.21663 (10)0.0124 (5)
S11.00718 (9)0.89723 (6)0.08375 (3)0.01409 (13)
O1G1.2225 (3)0.88624 (19)0.06914 (7)0.0208 (4)
C1G0.8946 (4)1.0283 (3)0.04598 (11)0.0233 (6)
H1G10.94491.12060.06150.035*
H1G20.74831.02430.04630.035*
H1G30.92881.01190.00930.035*
C2G0.8784 (4)0.7491 (3)0.04824 (11)0.0208 (6)
H2G10.90710.74200.01110.031*
H2G20.73340.75940.05010.031*
H2G30.92390.66430.06400.031*
S20.50038 (9)0.40349 (6)0.08343 (3)0.01460 (13)
O1H0.7177 (3)0.40828 (19)0.07026 (7)0.0206 (4)
C1H0.3754 (4)0.5325 (3)0.04717 (11)0.0221 (6)
H1H10.41340.62570.06450.033*
H1H20.22970.51940.04620.033*
H1H30.41450.52340.01090.033*
C2H0.3935 (4)0.2518 (3)0.04457 (11)0.0243 (6)
H2H10.43590.24770.00870.036*
H2H20.24650.25630.04270.036*
H2H30.43930.16800.06100.036*
O1W0.9185 (3)0.40010 (18)0.98237 (7)0.0207 (4)
H1W10.829 (4)0.414 (4)1.0040 (12)0.047 (11)*
H2W10.907 (5)0.466 (3)0.9622 (11)0.046 (11)*
O2W0.4243 (3)0.84838 (19)0.98024 (7)0.0217 (4)
H1W20.349 (5)0.853 (4)1.0051 (11)0.061 (13)*
H2W20.431 (5)0.7675 (18)0.9634 (12)0.041 (10)*
O3W0.5777 (3)0.94182 (17)0.12596 (7)0.0151 (4)
H1W30.458 (2)0.936 (3)0.1116 (11)0.029 (9)*
H2W30.598 (5)1.0221 (18)0.1433 (12)0.039 (10)*
O4W0.0735 (3)0.37916 (18)0.12416 (7)0.0155 (4)
H1W40.048 (2)0.375 (3)0.1109 (12)0.036 (10)*
H2W40.113 (5)0.314 (3)0.1433 (11)0.037 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0302 (11)0.0112 (8)0.0143 (9)0.0033 (8)0.0068 (8)0.0009 (7)
O20.0228 (10)0.0100 (8)0.0183 (10)0.0005 (7)0.0067 (8)0.0029 (7)
O30.0258 (10)0.0152 (9)0.0147 (9)0.0012 (7)0.0065 (8)0.0042 (7)
O40.0285 (11)0.0090 (8)0.0152 (9)0.0001 (7)0.0053 (8)0.0021 (7)
C10.0156 (13)0.0102 (11)0.0133 (12)0.0025 (9)0.0007 (10)0.0005 (9)
C20.0163 (13)0.0149 (12)0.0172 (13)0.0022 (10)0.0021 (10)0.0032 (10)
C30.0194 (14)0.0194 (13)0.0147 (13)0.0004 (10)0.0020 (11)0.0049 (10)
C40.0209 (14)0.0188 (13)0.0118 (12)0.0010 (10)0.0019 (10)0.0026 (10)
C50.0206 (13)0.0107 (11)0.0124 (12)0.0034 (9)0.0036 (10)0.0003 (9)
C60.0240 (14)0.0179 (13)0.0144 (13)0.0015 (11)0.0066 (11)0.0012 (10)
C70.0252 (15)0.0174 (13)0.0240 (14)0.0026 (11)0.0096 (12)0.0014 (11)
C80.0167 (13)0.0194 (13)0.0229 (14)0.0034 (10)0.0010 (11)0.0076 (11)
C90.0183 (13)0.0152 (12)0.0141 (13)0.0008 (10)0.0009 (10)0.0026 (10)
C100.0188 (13)0.0080 (11)0.0128 (12)0.0031 (9)0.0032 (10)0.0025 (9)
C110.0129 (12)0.0140 (12)0.0125 (12)0.0000 (9)0.0027 (9)0.0029 (9)
C120.0146 (12)0.0109 (11)0.0142 (12)0.0007 (9)0.0015 (10)0.0035 (9)
C130.0103 (12)0.0109 (11)0.0144 (12)0.0002 (9)0.0004 (9)0.0010 (9)
C140.0164 (13)0.0131 (12)0.0100 (12)0.0003 (9)0.0019 (10)0.0015 (9)
C150.0147 (12)0.0104 (11)0.0142 (12)0.0001 (9)0.0015 (10)0.0026 (9)
C160.0165 (13)0.0090 (11)0.0149 (13)0.0004 (9)0.0007 (10)0.0004 (9)
C170.0127 (12)0.0151 (12)0.0146 (13)0.0024 (9)0.0034 (10)0.0015 (10)
C180.0115 (12)0.0114 (12)0.0157 (13)0.0011 (9)0.0013 (10)0.0005 (9)
O1A0.0253 (10)0.0128 (9)0.0150 (9)0.0003 (7)0.0051 (8)0.0001 (7)
O2A0.0263 (10)0.0090 (8)0.0166 (9)0.0005 (7)0.0033 (8)0.0009 (7)
O3A0.0263 (10)0.0132 (9)0.0135 (9)0.0029 (7)0.0054 (8)0.0024 (7)
O4A0.0231 (10)0.0094 (8)0.0188 (10)0.0007 (7)0.0050 (8)0.0012 (7)
C1A0.0187 (13)0.0103 (11)0.0139 (12)0.0025 (9)0.0025 (10)0.0015 (9)
C2A0.0192 (13)0.0125 (12)0.0187 (13)0.0003 (10)0.0044 (11)0.0023 (10)
C3A0.0232 (15)0.0151 (13)0.0187 (14)0.0004 (11)0.0009 (11)0.0035 (10)
C4A0.0270 (15)0.0154 (12)0.0110 (12)0.0035 (10)0.0028 (11)0.0008 (10)
C5A0.0231 (13)0.0090 (11)0.0142 (12)0.0030 (10)0.0045 (10)0.0005 (9)
C6A0.0259 (15)0.0195 (13)0.0198 (14)0.0033 (11)0.0091 (12)0.0041 (11)
C7A0.0229 (15)0.0195 (13)0.0281 (15)0.0008 (11)0.0101 (12)0.0037 (11)
C8A0.0176 (14)0.0176 (13)0.0261 (15)0.0015 (10)0.0040 (11)0.0007 (11)
C9A0.0203 (14)0.0155 (12)0.0145 (13)0.0022 (10)0.0036 (11)0.0002 (10)
C10A0.0183 (13)0.0086 (11)0.0142 (12)0.0041 (9)0.0033 (10)0.0020 (9)
C11A0.0121 (12)0.0129 (11)0.0135 (12)0.0002 (9)0.0029 (10)0.0006 (9)
C12A0.0163 (13)0.0097 (11)0.0143 (12)0.0002 (9)0.0016 (10)0.0021 (9)
C13A0.0123 (12)0.0097 (11)0.0160 (13)0.0011 (9)0.0008 (10)0.0013 (9)
C14A0.0153 (12)0.0096 (11)0.0145 (12)0.0012 (9)0.0023 (10)0.0005 (9)
C15A0.0104 (12)0.0122 (11)0.0161 (13)0.0004 (9)0.0001 (10)0.0037 (9)
C16A0.0128 (12)0.0100 (11)0.0189 (13)0.0004 (9)0.0002 (10)0.0012 (10)
C17A0.0125 (12)0.0107 (11)0.0169 (13)0.0008 (9)0.0007 (10)0.0014 (10)
C18A0.0115 (12)0.0135 (12)0.0151 (13)0.0006 (9)0.0005 (10)0.0034 (10)
O1B0.0230 (10)0.0105 (8)0.0154 (9)0.0027 (7)0.0015 (8)0.0031 (7)
O2B0.0195 (9)0.0092 (8)0.0177 (9)0.0001 (7)0.0015 (7)0.0030 (7)
O3B0.0218 (10)0.0120 (8)0.0144 (9)0.0008 (7)0.0019 (7)0.0006 (7)
O4B0.0255 (10)0.0075 (8)0.0137 (9)0.0017 (7)0.0020 (7)0.0026 (7)
C1B0.0178 (13)0.0073 (11)0.0143 (12)0.0026 (9)0.0001 (10)0.0017 (9)
C2B0.0182 (13)0.0125 (12)0.0185 (13)0.0022 (10)0.0003 (10)0.0021 (10)
C3B0.0243 (15)0.0144 (13)0.0208 (14)0.0016 (11)0.0066 (11)0.0003 (10)
C4B0.0237 (14)0.0193 (13)0.0102 (12)0.0040 (11)0.0006 (11)0.0011 (10)
C5B0.0217 (14)0.0107 (12)0.0160 (13)0.0042 (10)0.0012 (11)0.0016 (10)
C6B0.0244 (15)0.0182 (13)0.0152 (13)0.0029 (11)0.0052 (11)0.0024 (10)
C7B0.0186 (14)0.0182 (13)0.0263 (15)0.0007 (11)0.0045 (11)0.0046 (11)
C8B0.0168 (13)0.0148 (12)0.0239 (14)0.0012 (10)0.0016 (11)0.0023 (10)
C9B0.0176 (13)0.0122 (12)0.0161 (13)0.0031 (9)0.0010 (10)0.0006 (10)
C10B0.0174 (13)0.0101 (11)0.0126 (12)0.0031 (9)0.0001 (10)0.0009 (9)
C11B0.0112 (12)0.0104 (11)0.0148 (12)0.0005 (9)0.0016 (10)0.0002 (9)
C12B0.0138 (12)0.0090 (11)0.0176 (13)0.0006 (9)0.0018 (10)0.0003 (9)
C13B0.0073 (11)0.0121 (11)0.0142 (12)0.0036 (9)0.0024 (9)0.0033 (9)
C14B0.0101 (12)0.0117 (11)0.0127 (12)0.0011 (9)0.0011 (9)0.0030 (9)
C15B0.0115 (12)0.0092 (11)0.0153 (12)0.0000 (9)0.0035 (10)0.0024 (9)
C16B0.0124 (12)0.0085 (11)0.0188 (13)0.0004 (9)0.0030 (10)0.0029 (9)
C17B0.0107 (12)0.0123 (11)0.0119 (12)0.0009 (9)0.0003 (9)0.0028 (9)
C18B0.0127 (12)0.0106 (11)0.0171 (13)0.0008 (9)0.0036 (10)0.0031 (10)
O1C0.0223 (10)0.0131 (9)0.0146 (9)0.0004 (7)0.0024 (7)0.0037 (7)
O2C0.0252 (10)0.0077 (8)0.0147 (9)0.0009 (7)0.0014 (8)0.0029 (7)
O3C0.0233 (10)0.0094 (8)0.0116 (9)0.0027 (7)0.0027 (7)0.0019 (7)
O4C0.0209 (10)0.0095 (8)0.0163 (9)0.0012 (7)0.0021 (7)0.0024 (7)
C1C0.0167 (13)0.0075 (10)0.0126 (12)0.0016 (9)0.0008 (10)0.0010 (9)
C2C0.0171 (13)0.0136 (12)0.0165 (13)0.0040 (10)0.0001 (10)0.0015 (10)
C3C0.0213 (14)0.0180 (13)0.0171 (13)0.0014 (11)0.0064 (11)0.0059 (10)
C4C0.0220 (14)0.0185 (12)0.0106 (12)0.0040 (10)0.0003 (10)0.0031 (10)
C5C0.0167 (13)0.0126 (12)0.0149 (13)0.0021 (10)0.0003 (10)0.0036 (10)
C6C0.0196 (14)0.0169 (13)0.0145 (13)0.0033 (10)0.0039 (11)0.0010 (10)
C7C0.0169 (13)0.0174 (13)0.0244 (14)0.0015 (10)0.0047 (11)0.0029 (11)
C8C0.0150 (13)0.0180 (13)0.0216 (14)0.0006 (10)0.0008 (11)0.0058 (11)
C9C0.0172 (13)0.0135 (12)0.0151 (13)0.0026 (10)0.0017 (10)0.0048 (10)
C10C0.0162 (12)0.0077 (10)0.0132 (12)0.0019 (9)0.0016 (10)0.0016 (9)
C11C0.0110 (12)0.0130 (11)0.0121 (12)0.0011 (9)0.0019 (9)0.0030 (9)
C12C0.0121 (12)0.0088 (11)0.0142 (12)0.0007 (9)0.0029 (10)0.0002 (9)
C13C0.0110 (12)0.0106 (11)0.0134 (12)0.0001 (9)0.0041 (9)0.0009 (9)
C14C0.0127 (12)0.0120 (11)0.0084 (12)0.0010 (9)0.0003 (9)0.0009 (9)
C15C0.0079 (11)0.0090 (11)0.0154 (12)0.0004 (9)0.0018 (9)0.0010 (9)
C16C0.0128 (12)0.0127 (12)0.0114 (12)0.0002 (9)0.0014 (10)0.0037 (9)
C17C0.0139 (12)0.0108 (11)0.0142 (13)0.0006 (9)0.0043 (10)0.0023 (9)
C18C0.0128 (12)0.0105 (11)0.0137 (12)0.0005 (9)0.0009 (10)0.0007 (9)
S10.0149 (3)0.0153 (3)0.0118 (3)0.0002 (2)0.0010 (2)0.0005 (2)
O1G0.0136 (9)0.0261 (10)0.0220 (10)0.0011 (8)0.0023 (8)0.0005 (8)
C1G0.0254 (15)0.0225 (14)0.0245 (15)0.0029 (11)0.0071 (12)0.0105 (11)
C2G0.0216 (14)0.0174 (13)0.0223 (14)0.0027 (10)0.0016 (11)0.0037 (11)
S20.0140 (3)0.0170 (3)0.0130 (3)0.0012 (2)0.0017 (2)0.0019 (2)
O1H0.0136 (9)0.0284 (10)0.0209 (10)0.0007 (8)0.0024 (7)0.0078 (8)
C1H0.0223 (15)0.0197 (13)0.0252 (15)0.0017 (11)0.0018 (12)0.0074 (11)
C2H0.0253 (15)0.0157 (13)0.0312 (16)0.0022 (11)0.0061 (12)0.0041 (11)
O1W0.0348 (12)0.0127 (9)0.0159 (10)0.0017 (8)0.0092 (9)0.0007 (8)
O2W0.0360 (12)0.0147 (9)0.0164 (10)0.0001 (8)0.0109 (9)0.0039 (8)
O3W0.0179 (10)0.0123 (9)0.0146 (9)0.0027 (7)0.0001 (8)0.0006 (7)
O4W0.0173 (10)0.0152 (9)0.0140 (9)0.0008 (7)0.0010 (8)0.0040 (7)
Geometric parameters (Å, º) top
O1—C171.318 (3)C4B—C5B1.412 (4)
O1—H10.8400C4B—H4B10.9500
O2—C171.212 (3)C5B—C6B1.418 (4)
O3—C181.218 (3)C5B—C10B1.434 (3)
O4—C181.324 (3)C6B—C7B1.367 (4)
O4—H40.8400C6B—H6B0.9500
C1—C21.368 (3)C7B—C8B1.408 (4)
C1—C101.427 (3)C7B—H7B0.9500
C1—C111.490 (3)C8B—C9B1.369 (4)
C2—C31.407 (3)C8B—H8B0.9500
C2—H20.9500C9B—C10B1.421 (3)
C3—C41.370 (4)C9B—H9B0.9500
C3—H30.9500C11B—C12B1.391 (3)
C4—C51.413 (4)C11B—C16B1.403 (3)
C4—H4A0.9500C12B—C13B1.394 (3)
C5—C61.423 (3)C12B—H12B0.9500
C5—C101.428 (3)C13B—C14B1.393 (3)
C6—C71.352 (4)C13B—C17B1.488 (3)
C6—H60.9500C14B—C15B1.396 (3)
C7—C81.422 (4)C14B—H14B0.9500
C7—H70.9500C15B—C16B1.389 (3)
C8—C91.365 (4)C15B—C18B1.492 (3)
C8—H80.9500C16B—H16B0.9500
C9—C101.421 (4)O1C—C17C1.220 (3)
C9—H90.9500O2C—C17C1.319 (3)
C11—C161.395 (3)O2C—H2C0.8400
C11—C121.399 (3)O3C—C18C1.321 (3)
C12—C131.391 (3)O3C—H3C0.8400
C12—H120.9500O4C—C18C1.223 (3)
C13—C141.389 (3)C1C—C2C1.368 (3)
C13—C171.496 (3)C1C—C10C1.432 (3)
C14—C151.396 (3)C1C—C11C1.492 (3)
C14—H140.9500C2C—C3C1.410 (4)
C15—C161.387 (3)C2C—H2C10.9500
C15—C181.491 (3)C3C—C4C1.365 (4)
C16—H160.9500C3C—H3C10.9500
O1A—C17A1.218 (3)C4C—C5C1.421 (4)
O2A—C17A1.321 (3)C4C—H4C0.9500
O2A—H2A0.8400C5C—C6C1.419 (4)
O3A—C18A1.320 (3)C5C—C10C1.427 (3)
O3A—H3A0.8400C6C—C7C1.362 (4)
O4A—C18A1.218 (3)C6C—H6C0.9500
C1A—C2A1.378 (4)C7C—C8C1.412 (4)
C1A—C10A1.430 (4)C7C—H7C0.9500
C1A—C11A1.498 (3)C8C—C9C1.365 (4)
C2A—C3A1.408 (4)C8C—H8C0.9500
C2A—H2A10.9500C9C—C10C1.426 (3)
C3A—C4A1.365 (4)C9C—H9C0.9500
C3A—H3A10.9500C11C—C16C1.384 (3)
C4A—C5A1.413 (4)C11C—C12C1.399 (3)
C4A—H4A10.9500C12C—C13C1.388 (3)
C5A—C6A1.419 (4)C12C—H12C0.9500
C5A—C10A1.429 (3)C13C—C14C1.394 (3)
C6A—C7A1.363 (4)C13C—C17C1.493 (3)
C6A—H6A0.9500C14C—C15C1.383 (3)
C7A—C8A1.412 (4)C14C—H14C0.9500
C7A—H7A0.9500C15C—C16C1.395 (3)
C8A—C9A1.359 (4)C15C—C18C1.491 (3)
C8A—H8A0.9500C16C—H16C0.9500
C9A—C10A1.422 (4)S1—O1G1.5229 (18)
C9A—H9A0.9500S1—C2G1.782 (3)
C11A—C16A1.393 (3)S1—C1G1.784 (3)
C11A—C12A1.399 (3)C1G—H1G10.9800
C12A—C13A1.390 (3)C1G—H1G20.9800
C12A—H12A0.9500C1G—H1G30.9800
C13A—C14A1.391 (3)C2G—H2G10.9800
C13A—C17A1.496 (3)C2G—H2G20.9800
C14A—C15A1.399 (3)C2G—H2G30.9800
C14A—H14A0.9500S2—O1H1.5242 (18)
C15A—C16A1.396 (3)S2—C1H1.780 (3)
C15A—C18A1.483 (3)S2—C2H1.785 (3)
C16A—H16A0.9500C1H—H1H10.9800
O1B—C17B1.321 (3)C1H—H1H20.9800
O1B—H1B0.8400C1H—H1H30.9800
O2B—C17B1.218 (3)C2H—H2H10.9800
O3B—C18B1.216 (3)C2H—H2H20.9800
O4B—C18B1.326 (3)C2H—H2H30.9800
O4B—H4B0.8400O1W—H1W10.856 (10)
C1B—C2B1.374 (3)O1W—H2W10.856 (10)
C1B—C10B1.435 (3)O2W—H1W20.846 (10)
C1B—C11B1.491 (3)O2W—H2W20.853 (10)
C2B—C3B1.419 (4)O3W—H1W30.847 (10)
C2B—H2B0.9500O3W—H2W30.853 (10)
C3B—C4B1.361 (4)O4W—H1W40.849 (10)
C3B—H3B0.9500O4W—H2W40.861 (10)
C17—O1—H1109.5C7B—C6B—C5B121.0 (3)
C18—O4—H4109.5C7B—C6B—H6B119.5
C2—C1—C10119.8 (2)C5B—C6B—H6B119.5
C2—C1—C11118.2 (2)C6B—C7B—C8B120.4 (2)
C10—C1—C11121.9 (2)C6B—C7B—H7B119.8
C1—C2—C3121.5 (2)C8B—C7B—H7B119.8
C1—C2—H2119.2C9B—C8B—C7B120.4 (2)
C3—C2—H2119.2C9B—C8B—H8B119.8
C4—C3—C2119.8 (2)C7B—C8B—H8B119.8
C4—C3—H3120.1C8B—C9B—C10B121.0 (2)
C2—C3—H3120.1C8B—C9B—H9B119.5
C3—C4—C5120.8 (2)C10B—C9B—H9B119.5
C3—C4—H4A119.6C9B—C10B—C5B118.4 (2)
C5—C4—H4A119.6C9B—C10B—C1B123.2 (2)
C4—C5—C6122.0 (2)C5B—C10B—C1B118.4 (2)
C4—C5—C10119.3 (2)C12B—C11B—C16B118.0 (2)
C6—C5—C10118.7 (2)C12B—C11B—C1B122.5 (2)
C7—C6—C5121.6 (2)C16B—C11B—C1B119.5 (2)
C7—C6—H6119.2C11B—C12B—C13B120.8 (2)
C5—C6—H6119.2C11B—C12B—H12B119.6
C6—C7—C8119.8 (2)C13B—C12B—H12B119.6
C6—C7—H7120.1C14B—C13B—C12B120.9 (2)
C8—C7—H7120.1C14B—C13B—C17B120.8 (2)
C9—C8—C7120.3 (2)C12B—C13B—C17B118.3 (2)
C9—C8—H8119.8C13B—C14B—C15B118.9 (2)
C7—C8—H8119.8C13B—C14B—H14B120.6
C8—C9—C10121.2 (2)C15B—C14B—H14B120.6
C8—C9—H9119.4C16B—C15B—C14B120.0 (2)
C10—C9—H9119.4C16B—C15B—C18B121.2 (2)
C9—C10—C1123.1 (2)C14B—C15B—C18B118.9 (2)
C9—C10—C5118.2 (2)C15B—C16B—C11B121.5 (2)
C1—C10—C5118.6 (2)C15B—C16B—H16B119.2
C16—C11—C12118.0 (2)C11B—C16B—H16B119.2
C16—C11—C1121.4 (2)O2B—C17B—O1B123.9 (2)
C12—C11—C1120.5 (2)O2B—C17B—C13B121.6 (2)
C13—C12—C11120.8 (2)O1B—C17B—C13B114.5 (2)
C13—C12—H12119.6O3B—C18B—O4B124.1 (2)
C11—C12—H12119.6O3B—C18B—C15B124.4 (2)
C14—C13—C12120.5 (2)O4B—C18B—C15B111.5 (2)
C14—C13—C17121.9 (2)C17C—O2C—H2C109.5
C12—C13—C17117.6 (2)C18C—O3C—H3C109.5
C13—C14—C15119.2 (2)C2C—C1C—C10C119.8 (2)
C13—C14—H14120.4C2C—C1C—C11C118.0 (2)
C15—C14—H14120.4C10C—C1C—C11C122.2 (2)
C16—C15—C14120.1 (2)C1C—C2C—C3C121.2 (2)
C16—C15—C18120.7 (2)C1C—C2C—H2C1119.4
C14—C15—C18119.2 (2)C3C—C2C—H2C1119.4
C15—C16—C11121.4 (2)C4C—C3C—C2C120.3 (2)
C15—C16—H16119.3C4C—C3C—H3C1119.8
C11—C16—H16119.3C2C—C3C—H3C1119.8
O2—C17—O1124.2 (2)C3C—C4C—C5C120.7 (2)
O2—C17—C13121.7 (2)C3C—C4C—H4C119.6
O1—C17—C13114.1 (2)C5C—C4C—H4C119.6
O3—C18—O4124.5 (2)C6C—C5C—C4C122.0 (2)
O3—C18—C15123.5 (2)C6C—C5C—C10C119.0 (2)
O4—C18—C15112.0 (2)C4C—C5C—C10C118.9 (2)
C17A—O2A—H2A109.5C7C—C6C—C5C121.3 (2)
C18A—O3A—H3A109.5C7C—C6C—H6C119.4
C2A—C1A—C10A119.6 (2)C5C—C6C—H6C119.4
C2A—C1A—C11A119.6 (2)C6C—C7C—C8C120.0 (2)
C10A—C1A—C11A120.7 (2)C6C—C7C—H7C120.0
C1A—C2A—C3A121.3 (2)C8C—C7C—H7C120.0
C1A—C2A—H2A1119.3C9C—C8C—C7C120.5 (2)
C3A—C2A—H2A1119.3C9C—C8C—H8C119.8
C4A—C3A—C2A120.0 (2)C7C—C8C—H8C119.8
C4A—C3A—H3A1120.0C8C—C9C—C10C121.2 (2)
C2A—C3A—H3A1120.0C8C—C9C—H9C119.4
C3A—C4A—C5A121.0 (2)C10C—C9C—H9C119.4
C3A—C4A—H4A1119.5C9C—C10C—C5C118.0 (2)
C5A—C4A—H4A1119.5C9C—C10C—C1C123.0 (2)
C4A—C5A—C6A121.6 (2)C5C—C10C—C1C119.0 (2)
C4A—C5A—C10A119.3 (2)C16C—C11C—C12C118.4 (2)
C6A—C5A—C10A119.1 (2)C16C—C11C—C1C120.8 (2)
C7A—C6A—C5A121.1 (3)C12C—C11C—C1C120.6 (2)
C7A—C6A—H6A119.4C13C—C12C—C11C120.7 (2)
C5A—C6A—H6A119.4C13C—C12C—H12C119.7
C6A—C7A—C8A119.8 (3)C11C—C12C—H12C119.7
C6A—C7A—H7A120.1C12C—C13C—C14C120.3 (2)
C8A—C7A—H7A120.1C12C—C13C—C17C120.5 (2)
C9A—C8A—C7A120.8 (3)C14C—C13C—C17C119.2 (2)
C9A—C8A—H8A119.6C15C—C14C—C13C119.3 (2)
C7A—C8A—H8A119.6C15C—C14C—H14C120.4
C8A—C9A—C10A121.2 (2)C13C—C14C—H14C120.4
C8A—C9A—H9A119.4C14C—C15C—C16C120.2 (2)
C10A—C9A—H9A119.4C14C—C15C—C18C121.7 (2)
C9A—C10A—C1A123.4 (2)C16C—C15C—C18C118.1 (2)
C9A—C10A—C5A117.9 (2)C11C—C16C—C15C121.1 (2)
C1A—C10A—C5A118.6 (2)C11C—C16C—H16C119.5
C16A—C11A—C12A118.3 (2)C15C—C16C—H16C119.5
C16A—C11A—C1A121.8 (2)O1C—C17C—O2C124.4 (2)
C12A—C11A—C1A119.9 (2)O1C—C17C—C13C123.5 (2)
C13A—C12A—C11A121.2 (2)O2C—C17C—C13C112.1 (2)
C13A—C12A—H12A119.4O4C—C18C—O3C123.5 (2)
C11A—C12A—H12A119.4O4C—C18C—C15C121.6 (2)
C12A—C13A—C14A120.4 (2)O3C—C18C—C15C114.9 (2)
C12A—C13A—C17A120.4 (2)O1G—S1—C2G105.32 (11)
C14A—C13A—C17A119.3 (2)O1G—S1—C1G105.23 (12)
C13A—C14A—C15A119.0 (2)C2G—S1—C1G98.15 (13)
C13A—C14A—H14A120.5S1—C1G—H1G1109.5
C15A—C14A—H14A120.5S1—C1G—H1G2109.5
C16A—C15A—C14A120.4 (2)H1G1—C1G—H1G2109.5
C16A—C15A—C18A118.8 (2)S1—C1G—H1G3109.5
C14A—C15A—C18A120.8 (2)H1G1—C1G—H1G3109.5
C11A—C16A—C15A120.8 (2)H1G2—C1G—H1G3109.5
C11A—C16A—H16A119.6S1—C2G—H2G1109.5
C15A—C16A—H16A119.6S1—C2G—H2G2109.5
O1A—C17A—O2A124.2 (2)H2G1—C2G—H2G2109.5
O1A—C17A—C13A123.8 (2)S1—C2G—H2G3109.5
O2A—C17A—C13A111.9 (2)H2G1—C2G—H2G3109.5
O4A—C18A—O3A124.0 (2)H2G2—C2G—H2G3109.5
O4A—C18A—C15A121.5 (2)O1H—S2—C1H104.86 (12)
O3A—C18A—C15A114.5 (2)O1H—S2—C2H104.87 (12)
C17B—O1B—H1B109.5C1H—S2—C2H98.30 (13)
C18B—O4B—H4B109.5S2—C1H—H1H1109.5
C2B—C1B—C10B119.4 (2)S2—C1H—H1H2109.5
C2B—C1B—C11B119.5 (2)H1H1—C1H—H1H2109.5
C10B—C1B—C11B121.0 (2)S2—C1H—H1H3109.5
C1B—C2B—C3B121.5 (2)H1H1—C1H—H1H3109.5
C1B—C2B—H2B119.2H1H2—C1H—H1H3109.5
C3B—C2B—H2B119.2S2—C2H—H2H1109.5
C4B—C3B—C2B119.9 (2)S2—C2H—H2H2109.5
C4B—C3B—H3B120.0H2H1—C2H—H2H2109.5
C2B—C3B—H3B120.0S2—C2H—H2H3109.5
C3B—C4B—C5B120.9 (2)H2H1—C2H—H2H3109.5
C3B—C4B—H4B1119.6H2H2—C2H—H2H3109.5
C5B—C4B—H4B1119.6H1W1—O1W—H2W1106 (3)
C4B—C5B—C6B121.6 (2)H1W2—O2W—H2W2115 (4)
C4B—C5B—C10B119.7 (2)H1W3—O3W—H2W3110 (3)
C6B—C5B—C10B118.7 (2)H1W4—O4W—H2W4117 (3)
C10—C1—C2—C31.8 (4)C10B—C1B—C2B—C3B3.1 (4)
C11—C1—C2—C3176.7 (2)C11B—C1B—C2B—C3B174.7 (2)
C1—C2—C3—C40.4 (4)C1B—C2B—C3B—C4B0.3 (4)
C2—C3—C4—C51.7 (4)C2B—C3B—C4B—C5B2.7 (4)
C3—C4—C5—C6178.0 (2)C3B—C4B—C5B—C6B177.2 (2)
C3—C4—C5—C100.9 (4)C3B—C4B—C5B—C10B1.7 (4)
C4—C5—C6—C7177.4 (3)C4B—C5B—C6B—C7B178.1 (3)
C10—C5—C6—C71.5 (4)C10B—C5B—C6B—C7B0.8 (4)
C5—C6—C7—C80.4 (4)C5B—C6B—C7B—C8B0.8 (4)
C6—C7—C8—C91.0 (4)C6B—C7B—C8B—C9B0.9 (4)
C7—C8—C9—C100.4 (4)C7B—C8B—C9B—C10B0.7 (4)
C8—C9—C10—C1179.5 (2)C8B—C9B—C10B—C5B2.3 (3)
C8—C9—C10—C52.3 (4)C8B—C9B—C10B—C1B179.5 (2)
C2—C1—C10—C9174.6 (2)C4B—C5B—C10B—C9B176.6 (2)
C11—C1—C10—C97.0 (4)C6B—C5B—C10B—C9B2.3 (3)
C2—C1—C10—C52.5 (3)C4B—C5B—C10B—C1B1.7 (3)
C11—C1—C10—C5175.9 (2)C6B—C5B—C10B—C1B179.4 (2)
C4—C5—C10—C9176.1 (2)C2B—C1B—C10B—C9B174.2 (2)
C6—C5—C10—C92.8 (3)C11B—C1B—C10B—C9B8.1 (4)
C4—C5—C10—C11.2 (3)C2B—C1B—C10B—C5B4.0 (3)
C6—C5—C10—C1179.9 (2)C11B—C1B—C10B—C5B173.7 (2)
C2—C1—C11—C16121.8 (3)C2B—C1B—C11B—C12B56.6 (3)
C10—C1—C11—C1656.7 (3)C10B—C1B—C11B—C12B125.7 (3)
C2—C1—C11—C1254.3 (3)C2B—C1B—C11B—C16B120.6 (3)
C10—C1—C11—C12127.3 (3)C10B—C1B—C11B—C16B57.1 (3)
C16—C11—C12—C130.1 (4)C16B—C11B—C12B—C13B1.1 (3)
C1—C11—C12—C13176.1 (2)C1B—C11B—C12B—C13B176.2 (2)
C11—C12—C13—C140.8 (4)C11B—C12B—C13B—C14B0.2 (3)
C11—C12—C13—C17178.6 (2)C11B—C12B—C13B—C17B179.0 (2)
C12—C13—C14—C151.0 (4)C12B—C13B—C14B—C15B1.1 (3)
C17—C13—C14—C15178.4 (2)C17B—C13B—C14B—C15B178.2 (2)
C13—C14—C15—C160.3 (4)C13B—C14B—C15B—C16B0.5 (3)
C13—C14—C15—C18178.6 (2)C13B—C14B—C15B—C18B178.7 (2)
C14—C15—C16—C110.7 (4)C14B—C15B—C16B—C11B0.8 (4)
C18—C15—C16—C11177.6 (2)C18B—C15B—C16B—C11B177.3 (2)
C12—C11—C16—C150.9 (4)C12B—C11B—C16B—C15B1.6 (4)
C1—C11—C16—C15175.3 (2)C1B—C11B—C16B—C15B175.7 (2)
C14—C13—C17—O2174.1 (2)C14B—C13B—C17B—O2B174.2 (2)
C12—C13—C17—O25.3 (4)C12B—C13B—C17B—O2B5.0 (3)
C14—C13—C17—O15.9 (3)C14B—C13B—C17B—O1B5.9 (3)
C12—C13—C17—O1174.6 (2)C12B—C13B—C17B—O1B174.9 (2)
C16—C15—C18—O3173.5 (2)C16B—C15B—C18B—O3B173.8 (2)
C14—C15—C18—O34.8 (4)C14B—C15B—C18B—O3B4.4 (4)
C16—C15—C18—O45.4 (3)C16B—C15B—C18B—O4B5.9 (3)
C14—C15—C18—O4176.3 (2)C14B—C15B—C18B—O4B176.0 (2)
C10A—C1A—C2A—C3A2.7 (3)C10C—C1C—C2C—C3C1.5 (4)
C11A—C1A—C2A—C3A174.1 (2)C11C—C1C—C2C—C3C177.6 (2)
C1A—C2A—C3A—C4A0.3 (4)C1C—C2C—C3C—C4C1.2 (4)
C2A—C3A—C4A—C5A2.8 (4)C2C—C3C—C4C—C5C2.5 (4)
C3A—C4A—C5A—C6A177.7 (2)C3C—C4C—C5C—C6C177.8 (2)
C3A—C4A—C5A—C10A2.1 (3)C3C—C4C—C5C—C10C1.1 (4)
C4A—C5A—C6A—C7A178.3 (2)C4C—C5C—C6C—C7C177.9 (2)
C10A—C5A—C6A—C7A1.5 (4)C10C—C5C—C6C—C7C1.1 (3)
C5A—C6A—C7A—C8A0.8 (4)C5C—C6C—C7C—C8C1.1 (4)
C6A—C7A—C8A—C9A1.8 (4)C6C—C7C—C8C—C9C1.7 (4)
C7A—C8A—C9A—C10A0.3 (4)C7C—C8C—C9C—C10C0.1 (4)
C8A—C9A—C10A—C1A179.8 (2)C8C—C9C—C10C—C5C2.0 (3)
C8A—C9A—C10A—C5A2.0 (3)C8C—C9C—C10C—C1C179.9 (2)
C2A—C1A—C10A—C9A174.5 (2)C6C—C5C—C10C—C9C2.6 (3)
C11A—C1A—C10A—C9A8.7 (3)C4C—C5C—C10C—C9C176.4 (2)
C2A—C1A—C10A—C5A3.3 (3)C6C—C5C—C10C—C1C179.5 (2)
C11A—C1A—C10A—C5A173.5 (2)C4C—C5C—C10C—C1C1.5 (3)
C4A—C5A—C10A—C9A176.9 (2)C2C—C1C—C10C—C9C175.0 (2)
C6A—C5A—C10A—C9A2.8 (3)C11C—C1C—C10C—C9C5.9 (3)
C4A—C5A—C10A—C1A1.0 (3)C2C—C1C—C10C—C5C2.8 (3)
C6A—C5A—C10A—C1A179.3 (2)C11C—C1C—C10C—C5C176.3 (2)
C2A—C1A—C11A—C16A56.6 (3)C2C—C1C—C11C—C16C54.5 (3)
C10A—C1A—C11A—C16A126.5 (3)C10C—C1C—C11C—C16C126.4 (2)
C2A—C1A—C11A—C12A120.0 (3)C2C—C1C—C11C—C12C121.9 (3)
C10A—C1A—C11A—C12A56.9 (3)C10C—C1C—C11C—C12C57.2 (3)
C16A—C11A—C12A—C13A1.1 (4)C16C—C11C—C12C—C13C1.2 (3)
C1A—C11A—C12A—C13A175.6 (2)C1C—C11C—C12C—C13C175.3 (2)
C11A—C12A—C13A—C14A1.2 (4)C11C—C12C—C13C—C14C0.5 (3)
C11A—C12A—C13A—C17A177.8 (2)C11C—C12C—C13C—C17C177.6 (2)
C12A—C13A—C14A—C15A0.0 (4)C12C—C13C—C14C—C15C0.8 (3)
C17A—C13A—C14A—C15A179.1 (2)C17C—C13C—C14C—C15C179.0 (2)
C13A—C14A—C15A—C16A1.3 (4)C13C—C14C—C15C—C16C1.5 (3)
C13A—C14A—C15A—C18A178.5 (2)C13C—C14C—C15C—C18C178.6 (2)
C12A—C11A—C16A—C15A0.1 (4)C12C—C11C—C16C—C15C0.5 (3)
C1A—C11A—C16A—C15A176.8 (2)C1C—C11C—C16C—C15C176.0 (2)
C14A—C15A—C16A—C11A1.4 (4)C14C—C15C—C16C—C11C0.9 (3)
C18A—C15A—C16A—C11A178.5 (2)C18C—C15C—C16C—C11C179.2 (2)
C12A—C13A—C17A—O1A172.8 (2)C12C—C13C—C17C—O1C174.8 (2)
C14A—C13A—C17A—O1A6.2 (4)C14C—C13C—C17C—O1C3.3 (4)
C12A—C13A—C17A—O2A6.2 (3)C12C—C13C—C17C—O2C4.4 (3)
C14A—C13A—C17A—O2A174.8 (2)C14C—C13C—C17C—O2C177.5 (2)
C16A—C15A—C18A—O4A5.8 (4)C14C—C15C—C18C—O4C174.9 (2)
C14A—C15A—C18A—O4A174.0 (2)C16C—C15C—C18C—O4C5.2 (3)
C16A—C15A—C18A—O3A174.2 (2)C14C—C15C—C18C—O3C5.1 (3)
C14A—C15A—C18A—O3A6.0 (3)C16C—C15C—C18C—O3C174.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.841.722.559 (2)175
O1B—H1B···O3W0.841.742.573 (2)168
O2A—H2A···O4Aii0.841.822.583 (2)151
O2C—H2C···O4Cii0.841.812.584 (2)152
O3A—H3A···O2Wiii0.841.732.565 (3)174
O3C—H3C···O4W0.841.722.561 (2)176
O4—H4···O2iii0.841.812.591 (2)154
O4B—H4B···O2Biii0.841.812.578 (2)150
O1W—H1W1···O1Hiv0.85 (3)1.92 (3)2.716 (3)155 (3)
O1W—H2W1···O3v0.85 (3)2.04 (3)2.858 (2)162 (3)
O2W—H1W2···O1Gvi0.85 (3)1.91 (3)2.742 (3)168 (3)
O2W—H2W2···O1A0.85 (2)2.03 (2)2.879 (2)174 (3)
O3W—H1W3···O1Gvii0.85 (2)1.85 (2)2.680 (3)165 (3)
O3W—H2W3···O3Bii0.85 (2)1.98 (2)2.824 (2)170 (3)
O4W—H1W4···O1Hvii0.85 (2)1.84 (2)2.656 (3)162 (3)
O4W—H2W4···O1Ciii0.86 (3)1.96 (3)2.808 (2)172 (3)
Symmetry codes: (i) x1, y+1, z; (ii) x, y+1, z; (iii) x, y1, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) x1, y, z+1; (vii) x1, y, z.

Experimental details

Crystal data
Chemical formula2C18H12O4·C2H6OS·2H2O
Mr698.72
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)6.6842 (4), 9.6173 (6), 25.4682 (15)
α, β, γ (°)95.780 (3), 95.669 (3), 90.028 (3)
V3)1620.82 (17)
Z2
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.18 × 0.17 × 0.09
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
39842, 15284, 12600
Rint0.043
(sin θ/λ)max1)0.663
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.100, 1.04
No. of reflections15284
No. of parameters945
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.29
Absolute structureFlack (1983), 7387 Friedel pairs
Absolute structure parameter0.03 (5)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.841.722.559 (2)175.0
O1B—H1B···O3W0.841.742.573 (2)168.0
O2A—H2A···O4Aii0.841.822.583 (2)151.0
O2C—H2C···O4Cii0.841.812.584 (2)152.0
O3A—H3A···O2Wiii0.841.732.565 (3)174.0
O3C—H3C···O4W0.841.722.561 (2)176.0
O4—H4···O2iii0.841.812.591 (2)154.0
O4B—H4B···O2Biii0.841.812.578 (2)150.0
O1W—H1W1···O1Hiv0.85 (3)1.92 (3)2.716 (3)155 (3)
O1W—H2W1···O3v0.85 (3)2.04 (3)2.858 (2)162 (3)
O2W—H1W2···O1Gvi0.85 (3)1.91 (3)2.742 (3)168 (3)
O2W—H2W2···O1A0.85 (2)2.03 (2)2.879 (2)174 (3)
O3W—H1W3···O1Gvii0.846 (17)1.85 (2)2.680 (3)165 (3)
O3W—H2W3···O3Bii0.85 (2)1.98 (2)2.824 (2)170 (3)
O4W—H1W4···O1Hvii0.848 (17)1.84 (2)2.656 (3)162 (3)
O4W—H2W4···O1Ciii0.86 (3)1.96 (3)2.808 (2)172 (3)
Symmetry codes: (i) x1, y+1, z; (ii) x, y+1, z; (iii) x, y1, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) x1, y, z+1; (vii) x1, y, z.
 

Acknowledgements

The authors thank the Deutsche Forschungsgemeinschaft (DFG) for financial support (SPP 1362/1).

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555–1573.  CrossRef CAS Web of Science
First citationBroutin, P.-E. & Colobert, F. (2005). Eur. J. Org. Chem. pp. 1113–1128.  Web of Science CSD CrossRef
First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBurrows, A. D. (2004). Struct. Bond. 108, 55–96.  Web of Science CrossRef CAS
First citationDerissen, J. L. (1974). Acta Cryst. B30, 2764–2765.  CSD CrossRef CAS IUCr Journals Web of Science
First citationDesiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. New York: Oxford University Press Inc.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationJames, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093–1099. Boca Raton: CRC Press.
First citationMazik, M. & König, A. (2006). J. Org. Chem. 71, 7854–7857.  Web of Science CrossRef PubMed CAS
First citationMiyaura, N., Yanagi, T. & Suzuki, A. (1981). Synth. Commun. 11, 513–519.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Chichester: Wiley.

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o912-o913
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds