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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 66| Part 8| August 2010| Page o2128
https://doi.org/10.1107/S1600536810029144

1-Ethyl­sulfinyl-2-(4-iodo­phen­yl)naphtho­[2,1-b]furan

Hong Dae Choi,a Pil Ja Seo,a Byeng Wha Sonb and Uk Leeb*

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 9 July 2010; accepted 21 July 2010; online 31 July 2010)

In the title compound, C20H15IO2S, the 4-iodo­phenyl ring makes a dihedral angle of 44.21 (7)° with the plane of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O and C—H⋯π inter­actions.

Related literature

For the pharmacological activity of naphtho­furan compounds, see: Einhorn et al. (1984[Einhorn, J., Demerseman, P., Royer, R., Cavier, R. & Gayral, P. (1984). Eur. J. Med. Chem. 19, 405-410.]); Hranjec et al. (2003[Hranjec, M., Grdisa, M., Pavelic, K., Boykin, D. W. & Karminski-Zamola, G. (2003). Farmaco, 58, 1319-1324.]); Mahadevan & Vaidya (2003[Mahadevan, K. M. & Vaidya, V. P. (2003). Indian J. Pharm. Sci. 65, 128-134.]). For the structures of related 2-aryl-1-(methyl­sulfin­yl)naphtho­[2,1-b]furan derivatives, see: Choi et al. (2006[Choi, H. D., Seo, P. J., Kang, B. W., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o5625-o5626.], 2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1012.]).

[Scheme 1]

Experimental

Crystal data

  • C20H15IO2S

  • Mr = 446.28

  • Monoclinic, P 21 /c

  • a = 9.1240 (5) Å

  • b = 12.4302 (6) Å

  • c = 15.8520 (8) Å

  • β = 105.899 (2)°

  • V = 1729.05 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.98 mm−1

  • T = 174 K

  • 0.27 × 0.23 × 0.10 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.619, Tmax = 0.825

  • 14865 measured reflections

  • 3937 independent reflections

  • 3511 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.084

  • S = 1.09

  • 3937 reflections

  • 218 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −1.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 4-iodo­phenyl ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C20—H20C⋯O2i 0.98 2.60 3.454 (4) 145
C19—H19B⋯Cgii 0.99 2.77 3.501 (3) 131
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. 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, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029144/ds2042sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029144/ds2042Isup2.hkl

checkCIF report


Comment top

Compounds containing a naphthofuran moiety show diverse pharmacological properties such as antibacterial, antitumor and anthelmintic activities (Einhorn et al., 1984, Hranjec et al., 2003, Mahadevan & Vaidya, 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 2-aryl-1-(methylsulfinyl)naphtho[2,1-b]furan analogues (Choi et al., 2006, 2010), we report the crystal structure of the title compound (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.044 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle formed by the naphthofuran plane and the 4-iodophenyl ring is 44.21 (7)°. The crystal packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the methyl H atom of the ethyl group and the oxygen of the S═O unit, with a C20—H20C···O2i (Table 1). The molecular packing (Fig. 2) is further stabilized by an intermolecular C—H···π interaction between the methylene H atom of the ethyl group and the 4-iodophenyl ring of an adjacent molecule, with a C19—H19B···Cgii (Table 1; Cg is the centroid of the C13–C18 4-iodophenyl ring).

Related literature top

For the pharmacological activity of naphthofuran compounds, see: Einhorn et al. (1984); Hranjec et al. (2003); Mahadevan & Vaidya (2003). For the structures of related 2-aryl-1-(methylsulfinyl)naphtho[2,1-b]furan derivatives, see: Choi et al. (2006, 2010).

Experimental top

77% 3-chloroperoxybenzoic acid (157 mg, 0.7 mmol) was added in small portions to a stirred solution of 1-ethylsulfanyl-2-(4-iodophenyl)naphtho [2,1-b]furan (301 mg, 0.7 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 440–441 K; Rf = 0.53 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, 0.99 Å for methylene, and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.

Structure description top

Compounds containing a naphthofuran moiety show diverse pharmacological properties such as antibacterial, antitumor and anthelmintic activities (Einhorn et al., 1984, Hranjec et al., 2003, Mahadevan & Vaidya, 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 2-aryl-1-(methylsulfinyl)naphtho[2,1-b]furan analogues (Choi et al., 2006, 2010), we report the crystal structure of the title compound (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.044 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle formed by the naphthofuran plane and the 4-iodophenyl ring is 44.21 (7)°. The crystal packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the methyl H atom of the ethyl group and the oxygen of the S═O unit, with a C20—H20C···O2i (Table 1). The molecular packing (Fig. 2) is further stabilized by an intermolecular C—H···π interaction between the methylene H atom of the ethyl group and the 4-iodophenyl ring of an adjacent molecule, with a C19—H19B···Cgii (Table 1; Cg is the centroid of the C13–C18 4-iodophenyl ring).

For the pharmacological activity of naphthofuran compounds, see: Einhorn et al. (1984); Hranjec et al. (2003); Mahadevan & Vaidya (2003). For the structures of related 2-aryl-1-(methylsulfinyl)naphtho[2,1-b]furan derivatives, see: Choi et al. (2006, 2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 1998); software used to prepare material for publication: SHELXL97.

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 spheres of arbitrary radius.
[Figure 2] Fig. 2. C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: ?? (i) - x + 1, - y + 2, - z + 1; (ii) - x + 1, - y + 1, - z +1.]
1-Ethylsulfinyl-2-(4-iodophenyl)naphtho[2,1-b]furan top
Crystal data top
C20H15IO2SF(000) = 880
Mr = 446.28Dx = 1.714 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.1240 (5) ÅCell parameters from 3937 reflections
b = 12.4302 (6) Åθ = 2.1–27.5°
c = 15.8520 (8) ŵ = 1.98 mm−1
β = 105.899 (2)°T = 174 K
V = 1729.05 (15) Å3Block, colourless
Z = 40.27 × 0.23 × 0.10 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3937 independent reflections
Radiation source: rotating anode3511 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.038
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 2.1°
φ and ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −16→13
Tmin = 0.619, Tmax = 0.825l = −20→19
14865 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.084H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0453P)2 + 0.6527P]
where P = (Fo2 + 2Fc2)/3
3937 reflections(Δ/σ)max = 0.001
218 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −1.28 e Å−3
Crystal data top
C20H15IO2SV = 1729.05 (15) Å3
Mr = 446.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.1240 (5) ŵ = 1.98 mm−1
b = 12.4302 (6) ÅT = 174 K
c = 15.8520 (8) Å0.27 × 0.23 × 0.10 mm
β = 105.899 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3937 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3511 reflections with I > 2σ(I)
Tmin = 0.619, Tmax = 0.825Rint = 0.038
14865 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.09Δρmax = 0.37 e Å−3
3937 reflectionsΔρmin = −1.28 e Å−3
218 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
I0.00380 (2)0.277333 (14)0.601089 (11)0.03776 (9)
S0.45899 (6)0.76556 (4)0.55355 (4)0.02160 (13)
O10.70925 (17)0.52550 (13)0.67638 (10)0.0239 (3)
O20.48599 (18)0.87424 (14)0.59467 (10)0.0285 (4)
C10.6068 (2)0.67815 (18)0.60936 (13)0.0205 (4)
C20.7714 (2)0.69096 (19)0.63592 (13)0.0213 (4)
C30.8780 (3)0.77275 (18)0.62844 (15)0.0238 (5)
C40.8389 (3)0.8777 (2)0.59683 (15)0.0275 (5)
H40.73480.89880.57980.033*
C50.9491 (3)0.9498 (2)0.59032 (17)0.0364 (6)
H50.92061.01960.56740.044*
C61.1048 (3)0.9209 (3)0.61747 (18)0.0406 (7)
H61.18070.97120.61280.049*
C71.1455 (3)0.8211 (3)0.65028 (16)0.0359 (6)
H71.25050.80260.66880.043*
C81.0358 (3)0.7438 (2)0.65766 (15)0.0289 (5)
C91.0814 (3)0.6397 (2)0.69298 (15)0.0311 (5)
H91.18680.62210.70950.037*
C100.9800 (3)0.5649 (2)0.70387 (15)0.0292 (5)
H101.01130.49670.72970.035*
C110.8256 (2)0.59444 (19)0.67454 (14)0.0230 (4)
C120.5766 (2)0.57813 (18)0.63581 (13)0.0206 (4)
C130.4390 (2)0.51475 (17)0.62874 (13)0.0203 (4)
C140.4302 (3)0.44819 (18)0.69846 (14)0.0242 (5)
H140.51060.44850.75120.029*
C150.3056 (3)0.38198 (19)0.69132 (15)0.0259 (5)
H150.30000.33720.73890.031*
C160.1890 (3)0.38172 (18)0.61392 (14)0.0234 (4)
C170.1941 (2)0.44740 (18)0.54422 (14)0.0234 (4)
H170.11270.44690.49180.028*
C180.3187 (2)0.51365 (18)0.55162 (14)0.0225 (4)
H180.32270.55890.50400.027*
C190.5111 (3)0.77015 (18)0.45098 (15)0.0274 (5)
H19A0.62120.78600.46300.033*
H19B0.49140.69920.42160.033*
C200.4199 (4)0.8559 (2)0.39126 (19)0.0442 (7)
H20A0.31110.83890.37790.066*
H20B0.45060.85850.33670.066*
H20C0.43910.92600.42060.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.04151 (13)0.03477 (14)0.03818 (12)−0.01862 (7)0.01291 (8)−0.00299 (6)
S0.0202 (3)0.0193 (3)0.0249 (3)0.0019 (2)0.0054 (2)−0.0001 (2)
O10.0217 (7)0.0252 (8)0.0241 (8)0.0026 (6)0.0052 (6)0.0041 (6)
O20.0315 (9)0.0215 (9)0.0344 (9)0.0020 (7)0.0120 (7)−0.0055 (6)
C10.0198 (10)0.0248 (11)0.0174 (9)0.0003 (9)0.0061 (7)−0.0011 (8)
C20.0201 (10)0.0270 (11)0.0173 (10)0.0010 (9)0.0059 (7)−0.0020 (8)
C30.0231 (11)0.0301 (13)0.0204 (10)−0.0055 (9)0.0097 (8)−0.0048 (9)
C40.0302 (11)0.0277 (12)0.0269 (11)−0.0060 (10)0.0118 (9)−0.0060 (9)
C50.0441 (15)0.0345 (15)0.0338 (13)−0.0145 (12)0.0158 (11)−0.0081 (11)
C60.0355 (14)0.0529 (18)0.0376 (14)−0.0217 (13)0.0169 (11)−0.0139 (13)
C70.0257 (12)0.0539 (18)0.0304 (13)−0.0126 (12)0.0114 (9)−0.0121 (12)
C80.0221 (10)0.0446 (14)0.0212 (11)−0.0045 (10)0.0077 (8)−0.0077 (10)
C90.0195 (10)0.0498 (16)0.0232 (11)0.0065 (11)0.0045 (8)−0.0061 (11)
C100.0234 (11)0.0410 (14)0.0221 (11)0.0094 (10)0.0044 (8)−0.0018 (10)
C110.0206 (10)0.0285 (12)0.0201 (10)0.0004 (9)0.0060 (7)−0.0013 (8)
C120.0205 (10)0.0217 (11)0.0193 (10)0.0020 (8)0.0048 (7)−0.0007 (8)
C130.0235 (10)0.0186 (10)0.0203 (10)0.0004 (8)0.0085 (8)−0.0001 (8)
C140.0264 (11)0.0254 (12)0.0198 (10)0.0012 (9)0.0045 (8)0.0012 (8)
C150.0330 (12)0.0230 (12)0.0232 (11)−0.0001 (9)0.0105 (9)0.0035 (9)
C160.0264 (11)0.0195 (11)0.0265 (11)−0.0031 (9)0.0110 (8)−0.0029 (9)
C170.0237 (10)0.0262 (11)0.0205 (10)0.0012 (9)0.0065 (8)−0.0024 (9)
C180.0261 (10)0.0236 (11)0.0191 (10)0.0006 (9)0.0083 (8)0.0029 (8)
C190.0360 (13)0.0250 (13)0.0207 (11)0.0006 (10)0.0067 (9)0.0010 (9)
C200.0500 (17)0.0410 (16)0.0373 (15)0.0042 (14)0.0045 (12)0.0157 (12)
Geometric parameters (Å, º) top
I—C162.096 (2)C9—C101.356 (4)
S—O21.4908 (18)C9—H90.9500
S—C11.769 (2)C10—C111.406 (3)
S—C191.816 (3)C10—H100.9500
O1—C111.371 (3)C12—C131.460 (3)
O1—C121.371 (2)C13—C141.401 (3)
C1—C121.364 (3)C13—C181.402 (3)
C1—C21.453 (3)C14—C151.382 (3)
C2—C111.376 (3)C14—H140.9500
C2—C31.434 (3)C15—C161.386 (3)
C3—C41.407 (3)C15—H150.9500
C3—C81.432 (3)C16—C171.385 (3)
C4—C51.372 (4)C17—C181.382 (3)
C4—H40.9500C17—H170.9500
C5—C61.413 (4)C18—H180.9500
C5—H50.9500C19—C201.515 (3)
C6—C71.358 (4)C19—H19A0.9900
C6—H60.9500C19—H19B0.9900
C7—C81.414 (4)C20—H20A0.9800
C7—H70.9500C20—H20B0.9800
C8—C91.426 (4)C20—H20C0.9800
O2—S—C1109.02 (10)O1—C11—C10122.8 (2)
O2—S—C19108.10 (10)C2—C11—C10125.5 (2)
C1—S—C1996.68 (11)C1—C12—O1110.63 (18)
C11—O1—C12106.32 (17)C1—C12—C13135.2 (2)
C12—C1—C2106.90 (19)O1—C12—C13114.11 (18)
C12—C1—S121.54 (16)C14—C13—C18118.8 (2)
C2—C1—S131.56 (17)C14—C13—C12119.50 (18)
C11—C2—C3119.1 (2)C18—C13—C12121.60 (19)
C11—C2—C1104.5 (2)C15—C14—C13120.7 (2)
C3—C2—C1136.4 (2)C15—C14—H14119.6
C4—C3—C8118.8 (2)C13—C14—H14119.6
C4—C3—C2125.1 (2)C14—C15—C16119.2 (2)
C8—C3—C2116.1 (2)C14—C15—H15120.4
C5—C4—C3120.8 (2)C16—C15—H15120.4
C5—C4—H4119.6C17—C16—C15121.3 (2)
C3—C4—H4119.6C17—C16—I119.33 (16)
C4—C5—C6120.5 (3)C15—C16—I119.35 (17)
C4—C5—H5119.7C18—C17—C16119.3 (2)
C6—C5—H5119.7C18—C17—H17120.3
C7—C6—C5119.7 (2)C16—C17—H17120.3
C7—C6—H6120.2C17—C18—C13120.6 (2)
C5—C6—H6120.2C17—C18—H18119.7
C6—C7—C8121.8 (3)C13—C18—H18119.7
C6—C7—H7119.1C20—C19—S110.37 (19)
C8—C7—H7119.1C20—C19—H19A109.6
C7—C8—C9120.8 (2)S—C19—H19A109.6
C7—C8—C3118.3 (3)C20—C19—H19B109.6
C9—C8—C3120.9 (2)S—C19—H19B109.6
C10—C9—C8122.4 (2)H19A—C19—H19B108.1
C10—C9—H9118.8C19—C20—H20A109.5
C8—C9—H9118.8C19—C20—H20B109.5
C9—C10—C11115.8 (2)H20A—C20—H20B109.5
C9—C10—H10122.1C19—C20—H20C109.5
C11—C10—H10122.1H20A—C20—H20C109.5
O1—C11—C2111.62 (18)H20B—C20—H20C109.5
O2—S—C1—C12132.48 (18)C3—C2—C11—O1−179.95 (19)
C19—S—C1—C12−115.73 (19)C1—C2—C11—O1−1.9 (2)
O2—S—C1—C2−47.7 (2)C3—C2—C11—C10−3.9 (3)
C19—S—C1—C264.1 (2)C1—C2—C11—C10174.1 (2)
C12—C1—C2—C111.5 (2)C9—C10—C11—O1176.2 (2)
S—C1—C2—C11−178.31 (17)C9—C10—C11—C20.6 (3)
C12—C1—C2—C3179.1 (2)C2—C1—C12—O1−0.7 (2)
S—C1—C2—C3−0.8 (4)S—C1—C12—O1179.19 (14)
C11—C2—C3—C4−174.8 (2)C2—C1—C12—C13−178.5 (2)
C1—C2—C3—C47.9 (4)S—C1—C12—C131.3 (4)
C11—C2—C3—C83.8 (3)C11—O1—C12—C1−0.5 (2)
C1—C2—C3—C8−173.5 (2)C11—O1—C12—C13177.89 (17)
C8—C3—C4—C52.9 (3)C1—C12—C13—C14−143.3 (3)
C2—C3—C4—C5−178.6 (2)O1—C12—C13—C1438.9 (3)
C3—C4—C5—C6−1.7 (4)C1—C12—C13—C1840.6 (4)
C4—C5—C6—C70.0 (4)O1—C12—C13—C18−137.2 (2)
C5—C6—C7—C80.5 (4)C18—C13—C14—C150.4 (3)
C6—C7—C8—C9−179.5 (2)C12—C13—C14—C15−175.7 (2)
C6—C7—C8—C30.7 (4)C13—C14—C15—C160.2 (4)
C4—C3—C8—C7−2.4 (3)C14—C15—C16—C17−0.9 (4)
C2—C3—C8—C7178.9 (2)C14—C15—C16—I177.76 (17)
C4—C3—C8—C9177.9 (2)C15—C16—C17—C180.7 (3)
C2—C3—C8—C9−0.8 (3)I—C16—C17—C18−177.86 (17)
C7—C8—C9—C10177.7 (2)C16—C17—C18—C130.0 (3)
C3—C8—C9—C10−2.6 (4)C14—C13—C18—C17−0.6 (3)
C8—C9—C10—C112.7 (3)C12—C13—C18—C17175.5 (2)
C12—O1—C11—C21.5 (2)O2—S—C19—C20−57.7 (2)
C12—O1—C11—C10−174.6 (2)C1—S—C19—C20−170.25 (19)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C13–C18 4-iodophenyl ring.
D—H···AD—HH···AD···AD—H···A
C20—H20C···O2i0.982.603.454 (4)145
C19—H19B···Cgii0.992.773.501 (3)131
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC20H15IO2S
Mr446.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)174
a, b, c (Å)9.1240 (5), 12.4302 (6), 15.8520 (8)
β (°) 105.899 (2)
V (Å3)1729.05 (15)
Z4
Radiation typeMo Kα
µ (mm−1)1.98
Crystal size (mm)0.27 × 0.23 × 0.10
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.619, 0.825
No. of measured, independent and
observed [I > 2σ(I)] reflections		14865, 3937, 3511
Rint0.038
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.084, 1.09
No. of reflections3937
No. of parameters218
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −1.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXL97.

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C13–C18 4-iodophenyl ring.
D—H···AD—HH···AD···AD—H···A
C20—H20C···O2i0.982.603.454 (4)145.1
C19—H19B···Cgii0.992.773.501 (3)131.1
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1.
 

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChoi, H. D., Seo, P. J., Kang, B. W., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o5625–o5626.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1012.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationEinhorn, J., Demerseman, P., Royer, R., Cavier, R. & Gayral, P. (1984). Eur. J. Med. Chem. 19, 405–410.  CAS Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationHranjec, M., Grdisa, M., Pavelic, K., Boykin, D. W. & Karminski-Zamola, G. (2003). Farmaco, 58, 1319–1324.  CrossRef PubMed CAS Google Scholar
 First citationMahadevan, K. M. & Vaidya, V. P. (2003). Indian J. Pharm. Sci. 65, 128–134.  CAS 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 66| Part 8| August 2010| Page o2128
https://doi.org/10.1107/S1600536810029144
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