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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-(3-Ethyl­sulfanyl-5-phenyl-1-benzo­furan-2-yl)acetic acid

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 14 August 2009; accepted 17 August 2009; online 22 August 2009)

The title compound, C18H16O3S, crystallizes with two symmetry-independent mol­ecules in the asymmetric unit. The phenyl rings are rotated out of the benzofuran planes, making dihedral angles of 43.38 (7) and 56.13 (6)° in the two mol­ecules. The carboxyl groups are involved in inversion-related inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by weak non-classical inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits inter­molecular C—H⋯π inter­actions, and two aromatic ππ inter­actions between the furan rings of neighbouring benzofuran systems; the centroid–centroid distances are 3.500 (3) and 3.605 (3) Å.

Related literature

For the crystal structures of similar 2-(5-aryl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2007a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3468.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o4331.]). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999[Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.]); Twyman & Allsop (1999[Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16O3S

  • Mr = 312.37

  • Monoclinic, P 21 /n

  • a = 12.4250 (7) Å

  • b = 11.7823 (7) Å

  • c = 21.2426 (13) Å

  • β = 93.021 (1)°

  • V = 3105.5 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 293 K

  • 0.40 × 0.40 × 0.20 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.918, Tmax = 0.958

  • 18961 measured reflections

  • 7033 independent reflections

  • 4490 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.02

  • 7033 reflections

  • 405 parameters

  • 2 restraints

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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2O⋯O3i 0.92 (2) 1.73 (2) 2.643 (2) 174 (3)
O5—H5O⋯O6ii 0.92 (2) 1.68 (2) 2.602 (2) 175 (4)
C6—H6⋯O5iii 0.93 2.57 3.461 (3) 161
C24—H24⋯O3 0.93 2.57 3.480 (3) 165
C12—H12⋯Cg4iv 0.93 2.91 3.561 (3) 131
C30—H30⋯Cg2v 0.93 2.80 3.506 (3) 133
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z; (iv) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]. Cg2 and Cg4 are the centroids of the C2–C7 and the C20–C25 benzene rings, respectively.

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT and SMART. 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The benzofuran ring systems have attracted considerable interest in the view of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). As a part of our ongoing studies on the synthesis and structures of 2-(5-aryl-1-benzofuran-2-yl)acetic acid analogues, the crystal structure of 2-(3-methylsulfanyl-5-phenyl-1-benzofuran-2-yl)acetic acid (Choi et al., 2007a) and 2-[5-(4-bromophenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetic acid (Choi et al., 2007b) have been described in the literature. Here we report the crystal structure of the title compound, which has two unique molecules in the asymmetric unit (further marked as A and B) (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.006 (2) Å for A, and 0.024 (2) Å for B, respectively, from the least-squares plane defined by the nine constituent atoms. In the title compound, the dihedral angles formed by the phenyl ring and the plane of the benzofuran fragment are 43.38 (7) in A and 56.13 (6)° in B, respectively. In the crystal structure, the carboxylic acid groups are involved in inversion-related intermolecular O–H···O hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by non-classical intermolecular C–H···O hydrogen bonds (Table 1 and Fig. 2). The crystal structure (Fig. 3) is further stabilized by intermolecular C–H···π interactions between the phenyl H atom and the benzene ring of the adjacent molecule, with a C12–H12···Cg4iv and a C30–H30···Cg2v (Table 1; Cg2 and Cg4 are the centroids of the C2-C7 and the C20-C25 benzene rings, respectively). The crystal packing (Fig. 3) also shows two aromatic ππ interactions between the furan rings of the adjacent benzofuran molecules, with a Cg1···Cg1vii and a Cg3···Cg3viii distances of 3.500 (3) and 3.605 (3) Å, respectively (Cg1 and Cg3 are the centroids of the C1/C2/C7/O1/C8 and the C19/C20/C25/O4/C26 furan rings, respectively).

Related literature top

For the crystal structures of similar 2-(5-aryl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2007a,b). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). Cg2 and Cg4 are the centroids of the C2–C7 and the C20–C25 benzene rings, respectively.

Experimental top

Ethyl 2-(3-ethylsulfanyl-5-phenyl-1-benzofuran-2-yl)acetate (374 mg, 1.1 mmol) was added to a solution of potassium hydroxide (309 mg, 5.5 mmol) in water (20 ml) and methanol (20 ml), and the mixture was refluxed for 6h, then cooled. Water was added, and the solution was extracted with dichloromethane. The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and then extracted with chloroform, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (ethyl acetate) to afford the title compound as a colorless solid [yield 80%, m.p. 413-414 K; Rf = 0.79 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in diisopropyl ether at room temperature.

Refinement top

Atoms H2O and H5O of the hydroxy groups was found in a difference Fourier map and were refined with an O–H distance restraint of 0.82 (3) Å. The other H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 Å for the aryl, 0.97 Å for the methylene, and 0.96 Å for the methyl H atoms with Uiso(H) = 1.2Ueq(C) for the aryl, methylene and methyl H atoms.

Computing details top

Data collection: SMART (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 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.
[Figure 2] Fig. 2. O–H···O and C–H···O hydrogen bonds (dotted lines) in the title compound. [Symmetry code: (i) - x, - y + 2, - z + 1; (ii) - x + 1, - y + 1, - z + 1; (iii) x, y + 1, z; (vi) x, y - 1, z.]
[Figure 3] Fig. 3. C–H···π and ππ interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (iv) x + 1/2, - y + 3/2, z + 1/2; (v) x - 1/2, - y + 3/2, z - 1/2; (vii) -x + 1, -y + 2, -z + 1; (viii) - x, -y + 1, -z + 1; (ix) - x + 1/2, y + 1/2, -z + 1/2; (x) -x + 1/2, y - 1/2, -z + 3/2.]
2-(3-Ethylsulfanyl-5-phenyl-1-benzofuran-2-yl)acetic acid top
Crystal data top
C18H16O3SF(000) = 1312
Mr = 312.37Dx = 1.336 Mg m3
Monoclinic, P21/nMelting point = 413–414 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.4250 (7) ÅCell parameters from 5569 reflections
b = 11.7823 (7) Åθ = 2.4–27.2°
c = 21.2426 (13) ŵ = 0.22 mm1
β = 93.021 (1)°T = 293 K
V = 3105.5 (3) Å3Block, colorless
Z = 80.40 × 0.40 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer
7033 independent reflections
Radiation source: fine-focus sealed tube4490 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.9°
ϕ and ω scansh = 1614
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1115
Tmin = 0.918, Tmax = 0.958l = 2227
18961 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)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0418P)2 + 1.3759P]
where P = (Fo2 + 2Fc2)/3
7033 reflections(Δ/σ)max < 0.001
405 parametersΔρmax = 0.27 e Å3
2 restraintsΔρmin = 0.35 e Å3
Crystal data top
C18H16O3SV = 3105.5 (3) Å3
Mr = 312.37Z = 8
Monoclinic, P21/nMo Kα radiation
a = 12.4250 (7) ŵ = 0.22 mm1
b = 11.7823 (7) ÅT = 293 K
c = 21.2426 (13) Å0.40 × 0.40 × 0.20 mm
β = 93.021 (1)°
Data collection top
Bruker SMART CCD
diffractometer
7033 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4490 reflections with I > 2σ(I)
Tmin = 0.918, Tmax = 0.958Rint = 0.051
18961 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0442 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.27 e Å3
7033 reflectionsΔρmin = 0.35 e Å3
405 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S10.42821 (4)0.74794 (5)0.56883 (3)0.03157 (15)
S20.09978 (5)0.26751 (5)0.45920 (3)0.03627 (16)
O10.35424 (11)1.06793 (13)0.52955 (7)0.0307 (3)
O20.12491 (13)0.98536 (16)0.54306 (7)0.0429 (4)
H2O0.054 (2)1.005 (3)0.5462 (16)0.102 (13)*
O30.07580 (12)0.94865 (15)0.44307 (7)0.0366 (4)
O40.13576 (11)0.60092 (13)0.46153 (7)0.0316 (4)
O50.42194 (12)0.46922 (13)0.56302 (7)0.0314 (4)
H5O0.493 (2)0.481 (3)0.5539 (17)0.116 (14)*
O60.37647 (12)0.50831 (14)0.46214 (7)0.0353 (4)
C10.41378 (16)0.89499 (18)0.56241 (9)0.0254 (5)
C20.47608 (16)0.98018 (18)0.59689 (9)0.0248 (5)
C30.55970 (16)0.97787 (18)0.64336 (9)0.0265 (5)
H30.58710.90910.65850.032*
C40.60141 (16)1.08000 (18)0.66661 (10)0.0271 (5)
C50.55883 (17)1.18297 (19)0.64317 (10)0.0330 (5)
H50.58741.25070.65910.040*
C60.47558 (18)1.1869 (2)0.59704 (11)0.0343 (5)
H60.44771.25540.58160.041*
C70.43644 (16)1.08408 (19)0.57530 (10)0.0282 (5)
C80.34212 (16)0.95192 (19)0.52408 (10)0.0275 (5)
C90.25729 (16)0.9119 (2)0.47742 (10)0.0311 (5)
H9A0.25750.82950.47760.037*
H9B0.27640.93630.43580.037*
C100.14441 (17)0.95190 (18)0.48781 (10)0.0272 (5)
C110.69182 (16)1.07951 (19)0.71553 (10)0.0287 (5)
C120.69211 (17)1.0048 (2)0.76654 (10)0.0313 (5)
H120.63490.95470.77020.038*
C130.77631 (18)1.0042 (2)0.81172 (10)0.0363 (6)
H130.77490.95450.84570.044*
C140.86258 (19)1.0771 (2)0.80665 (11)0.0412 (6)
H140.91951.07620.83690.049*
C150.86381 (19)1.1513 (2)0.75639 (11)0.0440 (6)
H150.92181.20030.75280.053*
C160.77908 (18)1.1532 (2)0.71117 (11)0.0369 (6)
H160.78041.20390.67770.044*
C170.3695 (2)0.7258 (2)0.64445 (11)0.0388 (6)
H17A0.37260.64560.65470.047*
H17B0.41220.76620.67680.047*
C180.2544 (2)0.7653 (2)0.64531 (12)0.0441 (6)
H18A0.21130.72460.61400.053*
H18B0.25090.84510.63630.053*
H18C0.22760.75130.68620.053*
C190.09835 (16)0.41459 (19)0.44545 (10)0.0272 (5)
C200.03217 (15)0.47991 (18)0.40052 (9)0.0249 (5)
C210.04696 (15)0.45394 (18)0.35359 (9)0.0260 (5)
H210.06360.37890.34360.031*
C220.10028 (16)0.54269 (19)0.32209 (9)0.0262 (5)
C230.07088 (17)0.65529 (19)0.33561 (10)0.0300 (5)
H230.10650.71350.31350.036*
C240.00971 (17)0.68284 (19)0.38098 (10)0.0323 (5)
H240.02980.75750.38940.039*
C250.05787 (16)0.59262 (19)0.41258 (9)0.0268 (5)
C260.15723 (16)0.4906 (2)0.48009 (10)0.0294 (5)
C270.23707 (16)0.4758 (2)0.53380 (10)0.0343 (5)
H27A0.22630.40180.55240.041*
H27B0.22320.53240.56550.041*
C280.35276 (17)0.48548 (18)0.51715 (9)0.0258 (5)
C290.19404 (16)0.51884 (19)0.27720 (10)0.0279 (5)
C300.18684 (18)0.44420 (19)0.22683 (10)0.0316 (5)
H300.12140.40940.21980.038*
C310.27602 (19)0.4213 (2)0.18717 (11)0.0384 (6)
H310.27000.37270.15310.046*
C320.37435 (19)0.4708 (2)0.19823 (11)0.0409 (6)
H320.43470.45410.17210.049*
C330.38292 (18)0.5449 (2)0.24798 (11)0.0390 (6)
H330.44890.57830.25530.047*
C340.29342 (17)0.5695 (2)0.28696 (10)0.0339 (5)
H340.29940.62030.32010.041*
C350.1906 (2)0.2174 (2)0.40061 (12)0.0438 (6)
H35A0.24620.27400.39560.053*
H35B0.22560.14850.41610.053*
C360.1365 (3)0.1937 (3)0.33772 (13)0.0640 (8)
H36A0.10250.26160.32160.077*
H36B0.08300.13570.34180.077*
H36C0.18900.16850.30930.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0307 (3)0.0256 (3)0.0383 (3)0.0037 (2)0.0005 (2)0.0017 (2)
S20.0380 (3)0.0335 (3)0.0378 (3)0.0016 (3)0.0059 (3)0.0099 (3)
O10.0293 (8)0.0282 (9)0.0342 (8)0.0021 (7)0.0007 (6)0.0067 (7)
O20.0287 (9)0.0706 (13)0.0294 (9)0.0054 (9)0.0003 (7)0.0133 (8)
O30.0310 (9)0.0518 (11)0.0262 (8)0.0020 (8)0.0051 (7)0.0036 (7)
O40.0277 (8)0.0346 (9)0.0319 (8)0.0012 (7)0.0023 (6)0.0039 (7)
O50.0272 (8)0.0363 (9)0.0304 (8)0.0015 (7)0.0027 (7)0.0053 (7)
O60.0303 (8)0.0525 (11)0.0232 (8)0.0004 (8)0.0012 (6)0.0001 (7)
C10.0229 (10)0.0266 (11)0.0271 (11)0.0009 (9)0.0043 (8)0.0016 (9)
C20.0205 (10)0.0260 (12)0.0285 (11)0.0001 (9)0.0064 (8)0.0032 (9)
C30.0228 (10)0.0275 (12)0.0294 (11)0.0022 (9)0.0046 (9)0.0029 (9)
C40.0233 (10)0.0299 (12)0.0289 (11)0.0010 (9)0.0072 (9)0.0011 (9)
C50.0308 (12)0.0284 (12)0.0400 (13)0.0057 (10)0.0038 (10)0.0017 (10)
C60.0357 (13)0.0258 (12)0.0419 (13)0.0027 (10)0.0052 (10)0.0066 (10)
C70.0241 (11)0.0309 (12)0.0296 (12)0.0004 (10)0.0026 (9)0.0042 (9)
C80.0241 (11)0.0300 (12)0.0288 (11)0.0022 (9)0.0049 (9)0.0025 (9)
C90.0290 (11)0.0367 (13)0.0277 (12)0.0031 (10)0.0010 (9)0.0009 (10)
C100.0298 (11)0.0277 (12)0.0241 (11)0.0016 (9)0.0003 (9)0.0024 (9)
C110.0242 (11)0.0325 (13)0.0297 (12)0.0016 (9)0.0045 (9)0.0065 (9)
C120.0266 (11)0.0367 (13)0.0311 (12)0.0024 (10)0.0070 (9)0.0048 (10)
C130.0341 (13)0.0451 (15)0.0299 (12)0.0029 (11)0.0033 (10)0.0042 (11)
C140.0299 (12)0.0603 (18)0.0331 (13)0.0016 (12)0.0021 (10)0.0076 (12)
C150.0303 (13)0.0567 (17)0.0449 (15)0.0143 (12)0.0022 (11)0.0062 (13)
C160.0329 (12)0.0422 (15)0.0361 (13)0.0069 (11)0.0052 (10)0.0010 (11)
C170.0535 (15)0.0279 (13)0.0345 (13)0.0050 (11)0.0033 (11)0.0058 (10)
C180.0526 (16)0.0373 (15)0.0439 (14)0.0085 (12)0.0185 (12)0.0026 (11)
C190.0227 (10)0.0312 (12)0.0282 (11)0.0026 (9)0.0057 (9)0.0036 (9)
C200.0191 (10)0.0294 (12)0.0268 (11)0.0028 (9)0.0061 (8)0.0011 (9)
C210.0218 (10)0.0270 (11)0.0296 (11)0.0031 (9)0.0063 (9)0.0010 (9)
C220.0226 (10)0.0315 (12)0.0249 (11)0.0013 (9)0.0056 (8)0.0021 (9)
C230.0301 (11)0.0278 (12)0.0323 (12)0.0050 (10)0.0041 (9)0.0052 (9)
C240.0312 (12)0.0268 (12)0.0388 (13)0.0014 (10)0.0023 (10)0.0018 (10)
C250.0213 (10)0.0332 (13)0.0262 (11)0.0010 (9)0.0028 (8)0.0027 (9)
C260.0228 (11)0.0367 (13)0.0289 (12)0.0011 (10)0.0038 (9)0.0016 (10)
C270.0271 (11)0.0487 (15)0.0270 (12)0.0003 (11)0.0007 (9)0.0008 (10)
C280.0280 (11)0.0235 (11)0.0255 (11)0.0008 (9)0.0023 (9)0.0024 (9)
C290.0261 (11)0.0312 (12)0.0265 (11)0.0024 (9)0.0024 (9)0.0092 (9)
C300.0294 (12)0.0332 (13)0.0325 (12)0.0028 (10)0.0049 (10)0.0045 (10)
C310.0448 (14)0.0383 (14)0.0317 (13)0.0102 (12)0.0009 (11)0.0041 (10)
C320.0331 (13)0.0523 (17)0.0364 (14)0.0140 (12)0.0085 (10)0.0134 (12)
C330.0247 (12)0.0546 (17)0.0375 (14)0.0010 (11)0.0010 (10)0.0135 (12)
C340.0301 (12)0.0417 (14)0.0301 (12)0.0024 (11)0.0028 (10)0.0067 (10)
C350.0431 (14)0.0326 (14)0.0567 (16)0.0088 (12)0.0122 (12)0.0058 (12)
C360.082 (2)0.058 (2)0.0526 (18)0.0103 (17)0.0174 (16)0.0032 (15)
Geometric parameters (Å, º) top
S1—C11.746 (2)C16—H160.9300
S1—C171.818 (2)C17—C181.505 (3)
S2—C191.757 (2)C17—H17A0.9700
S2—C351.822 (2)C17—H17B0.9700
O1—C81.379 (3)C18—H18A0.9600
O1—C71.385 (2)C18—H18B0.9600
O2—C101.273 (2)C18—H18C0.9600
O2—H2O0.92 (2)C19—C261.350 (3)
O3—C101.243 (2)C19—C201.448 (3)
O4—C261.380 (3)C20—C251.387 (3)
O4—C251.386 (2)C20—C211.397 (3)
O5—C281.279 (2)C21—C221.390 (3)
O5—H5O0.92 (2)C21—H210.9300
O6—C281.249 (2)C22—C231.402 (3)
C1—C81.353 (3)C22—C291.493 (3)
C1—C21.443 (3)C23—C241.391 (3)
C2—C71.388 (3)C23—H230.9300
C2—C31.395 (3)C24—C251.377 (3)
C3—C41.390 (3)C24—H240.9300
C3—H30.9300C26—C271.482 (3)
C4—C51.404 (3)C27—C281.503 (3)
C4—C111.490 (3)C27—H27A0.9700
C5—C61.388 (3)C27—H27B0.9700
C5—H50.9300C29—C301.392 (3)
C6—C71.376 (3)C29—C341.397 (3)
C6—H60.9300C30—C311.383 (3)
C8—C91.485 (3)C30—H300.9300
C9—C101.507 (3)C31—C321.385 (3)
C9—H9A0.9700C31—H310.9300
C9—H9B0.9700C32—C331.379 (3)
C11—C161.395 (3)C32—H320.9300
C11—C121.396 (3)C33—C341.382 (3)
C12—C131.382 (3)C33—H330.9300
C12—H120.9300C34—H340.9300
C13—C141.382 (3)C35—C361.490 (4)
C13—H130.9300C35—H35A0.9700
C14—C151.380 (4)C35—H35B0.9700
C14—H140.9300C36—H36A0.9600
C15—C161.387 (3)C36—H36B0.9600
C15—H150.9300C36—H36C0.9600
C1—S1—C1799.60 (10)C17—C18—H18C109.5
C19—S2—C35101.98 (11)H18A—C18—H18C109.5
C8—O1—C7105.57 (16)H18B—C18—H18C109.5
C10—O2—H2O112 (2)C26—C19—C20106.23 (19)
C26—O4—C25105.34 (16)C26—C19—S2124.28 (17)
C28—O5—H5O115 (2)C20—C19—S2129.35 (16)
C8—C1—C2106.20 (19)C25—C20—C21119.23 (19)
C8—C1—S1126.92 (17)C25—C20—C19105.66 (18)
C2—C1—S1126.88 (16)C21—C20—C19135.1 (2)
C7—C2—C3119.26 (19)C22—C21—C20118.6 (2)
C7—C2—C1105.91 (18)C22—C21—H21120.7
C3—C2—C1134.8 (2)C20—C21—H21120.7
C4—C3—C2119.0 (2)C21—C22—C23120.04 (19)
C4—C3—H3120.5C21—C22—C29120.12 (19)
C2—C3—H3120.5C23—C22—C29119.69 (19)
C3—C4—C5119.69 (19)C24—C23—C22122.2 (2)
C3—C4—C11119.8 (2)C24—C23—H23118.9
C5—C4—C11120.5 (2)C22—C23—H23118.9
C6—C5—C4122.2 (2)C25—C24—C23115.9 (2)
C6—C5—H5118.9C25—C24—H24122.1
C4—C5—H5118.9C23—C24—H24122.1
C7—C6—C5116.4 (2)C24—C25—O4125.42 (19)
C7—C6—H6121.8C24—C25—C20124.01 (19)
C5—C6—H6121.8O4—C25—C20110.56 (18)
C6—C7—O1126.2 (2)C19—C26—O4112.21 (18)
C6—C7—C2123.5 (2)C19—C26—C27131.6 (2)
O1—C7—C2110.25 (18)O4—C26—C27116.21 (19)
C1—C8—O1112.04 (19)C26—C27—C28114.82 (18)
C1—C8—C9131.7 (2)C26—C27—H27A108.6
O1—C8—C9116.21 (18)C28—C27—H27A108.6
C8—C9—C10115.85 (18)C26—C27—H27B108.6
C8—C9—H9A108.3C28—C27—H27B108.6
C10—C9—H9A108.3H27A—C27—H27B107.5
C8—C9—H9B108.3O6—C28—O5124.23 (19)
C10—C9—H9B108.3O6—C28—C27120.81 (18)
H9A—C9—H9B107.4O5—C28—C27114.97 (18)
O3—C10—O2123.9 (2)C30—C29—C34118.5 (2)
O3—C10—C9118.97 (18)C30—C29—C22122.04 (19)
O2—C10—C9117.10 (18)C34—C29—C22119.4 (2)
C16—C11—C12118.3 (2)C31—C30—C29120.7 (2)
C16—C11—C4120.7 (2)C31—C30—H30119.7
C12—C11—C4120.99 (19)C29—C30—H30119.7
C13—C12—C11120.9 (2)C30—C31—C32120.0 (2)
C13—C12—H12119.6C30—C31—H31120.0
C11—C12—H12119.6C32—C31—H31120.0
C12—C13—C14120.3 (2)C33—C32—C31120.1 (2)
C12—C13—H13119.9C33—C32—H32120.0
C14—C13—H13119.9C31—C32—H32120.0
C15—C14—C13119.6 (2)C32—C33—C34120.0 (2)
C15—C14—H14120.2C32—C33—H33120.0
C13—C14—H14120.2C34—C33—H33120.0
C14—C15—C16120.4 (2)C33—C34—C29120.8 (2)
C14—C15—H15119.8C33—C34—H34119.6
C16—C15—H15119.8C29—C34—H34119.6
C15—C16—C11120.5 (2)C36—C35—S2114.02 (19)
C15—C16—H16119.7C36—C35—H35A108.7
C11—C16—H16119.7S2—C35—H35A108.7
C18—C17—S1113.11 (16)C36—C35—H35B108.7
C18—C17—H17A109.0S2—C35—H35B108.7
S1—C17—H17A109.0H35A—C35—H35B107.6
C18—C17—H17B109.0C35—C36—H36A109.5
S1—C17—H17B109.0C35—C36—H36B109.5
H17A—C17—H17B107.8H36A—C36—H36B109.5
C17—C18—H18A109.5C35—C36—H36C109.5
C17—C18—H18B109.5H36A—C36—H36C109.5
H18A—C18—H18B109.5H36B—C36—H36C109.5
C17—S1—C1—C8106.3 (2)C35—S2—C19—C2699.5 (2)
C17—S1—C1—C273.8 (2)C35—S2—C19—C2085.5 (2)
C8—C1—C2—C70.7 (2)C26—C19—C20—C250.1 (2)
S1—C1—C2—C7179.23 (16)S2—C19—C20—C25175.61 (16)
C8—C1—C2—C3178.9 (2)C26—C19—C20—C21177.7 (2)
S1—C1—C2—C31.2 (3)S2—C19—C20—C212.1 (4)
C7—C2—C3—C40.3 (3)C25—C20—C21—C222.4 (3)
C1—C2—C3—C4179.8 (2)C19—C20—C21—C22175.0 (2)
C2—C3—C4—C50.1 (3)C20—C21—C22—C232.9 (3)
C2—C3—C4—C11179.07 (18)C20—C21—C22—C29172.70 (18)
C3—C4—C5—C60.0 (3)C21—C22—C23—C241.2 (3)
C11—C4—C5—C6179.2 (2)C29—C22—C23—C24174.40 (19)
C4—C5—C6—C70.1 (3)C22—C23—C24—C251.0 (3)
C5—C6—C7—O1179.84 (19)C23—C24—C25—O4176.59 (18)
C5—C6—C7—C20.3 (3)C23—C24—C25—C201.5 (3)
C8—O1—C7—C6179.2 (2)C26—O4—C25—C24177.8 (2)
C8—O1—C7—C21.2 (2)C26—O4—C25—C200.6 (2)
C3—C2—C7—C60.4 (3)C21—C20—C25—C240.2 (3)
C1—C2—C7—C6180.0 (2)C19—C20—C25—C24177.96 (19)
C3—C2—C7—O1180.00 (17)C21—C20—C25—O4178.51 (17)
C1—C2—C7—O10.3 (2)C19—C20—C25—O40.4 (2)
C2—C1—C8—O11.5 (2)C20—C19—C26—O40.3 (2)
S1—C1—C8—O1178.41 (14)S2—C19—C26—O4176.24 (14)
C2—C1—C8—C9179.7 (2)C20—C19—C26—C27178.4 (2)
S1—C1—C8—C90.2 (3)S2—C19—C26—C272.5 (3)
C7—O1—C8—C11.7 (2)C25—O4—C26—C190.5 (2)
C7—O1—C8—C9179.80 (17)C25—O4—C26—C27178.42 (17)
C1—C8—C9—C10122.9 (2)C19—C26—C27—C28102.0 (3)
O1—C8—C9—C1058.9 (3)O4—C26—C27—C2879.3 (2)
C8—C9—C10—O3160.6 (2)C26—C27—C28—O62.4 (3)
C8—C9—C10—O220.7 (3)C26—C27—C28—O5177.9 (2)
C3—C4—C11—C16136.0 (2)C21—C22—C29—C3055.1 (3)
C5—C4—C11—C1643.2 (3)C23—C22—C29—C30129.3 (2)
C3—C4—C11—C1243.3 (3)C21—C22—C29—C34122.6 (2)
C5—C4—C11—C12137.5 (2)C23—C22—C29—C3453.0 (3)
C16—C11—C12—C130.4 (3)C34—C29—C30—C310.4 (3)
C4—C11—C12—C13179.7 (2)C22—C29—C30—C31178.1 (2)
C11—C12—C13—C140.8 (3)C29—C30—C31—C321.5 (3)
C12—C13—C14—C150.5 (4)C30—C31—C32—C331.4 (3)
C13—C14—C15—C160.1 (4)C31—C32—C33—C340.2 (4)
C14—C15—C16—C110.5 (4)C32—C33—C34—C290.9 (3)
C12—C11—C16—C150.3 (3)C30—C29—C34—C330.8 (3)
C4—C11—C16—C15179.1 (2)C22—C29—C34—C33176.9 (2)
C1—S1—C17—C1859.18 (19)C19—S2—C35—C3686.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O3i0.92 (2)1.73 (2)2.643 (2)174 (3)
O5—H5O···O6ii0.92 (2)1.68 (2)2.602 (2)175 (4)
C6—H6···O5iii0.932.573.461 (3)161
C24—H24···O30.932.573.480 (3)165
C12—H12···Cg4iv0.932.913.561 (3)131
C30—H30···Cg2v0.932.803.506 (3)133
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x+1/2, y+3/2, z+1/2; (v) x1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC18H16O3S
Mr312.37
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)12.4250 (7), 11.7823 (7), 21.2426 (13)
β (°) 93.021 (1)
V3)3105.5 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.40 × 0.40 × 0.20
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.918, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
18961, 7033, 4490
Rint0.051
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.116, 1.02
No. of reflections7033
No. of parameters405
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.35

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O3i0.92 (2)1.73 (2)2.643 (2)174 (3)
O5—H5O···O6ii0.92 (2)1.68 (2)2.602 (2)175 (4)
C6—H6···O5iii0.932.573.461 (3)161.1
C24—H24···O30.932.573.480 (3)164.7
C12—H12···Cg4iv0.932.913.561 (3)130.8
C30—H30···Cg2v0.932.803.506 (3)133.3
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1, z; (iv) x+1/2, y+3/2, z+1/2; (v) x1/2, y+3/2, z1/2.
 

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3468.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o4331.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationHowlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTwyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384.  Web of Science CrossRef CAS

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