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

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ISSN: 2056-9890

3-Cyclo­hexyl­sulfonyl-5-iodo-2,7-di­methyl-1-benzo­furan

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 6 July 2011; accepted 8 July 2011; online 16 July 2011)

In the title compound, C16H19IO3S, the cyclo­hexyl ring adopts a chair conformation. In the crystal, pairs of inter­molecular I⋯O contacts [3.269 (2) Å] link the mol­ecules into inversion dimers. These dimers are further stabilized by a slipped ππ inter­action between the benzene and furan rings of adjacent mol­ecules [centroid–centroid distance = 3.701 (3) Å, inter­planar distance = 3.372 (3) Å and slippage = 1.525 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For structural studies of related 3-cyclo­hexyl­sulfonyl-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o542.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o828.],c[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011c). Acta Cryst. E67, o847.]). For a review on halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19IO3S

  • Mr = 418.27

  • Triclinic, [P \overline 1]

  • a = 6.8643 (2) Å

  • b = 8.4981 (2) Å

  • c = 14.2323 (3) Å

  • α = 102.512 (1)°

  • β = 99.846 (1)°

  • γ = 92.092 (1)°

  • V = 796.23 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.15 mm−1

  • T = 173 K

  • 0.24 × 0.16 × 0.14 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 = 0.629, Tmax = 0.759

  • 15021 measured reflections

  • 3997 independent reflections

  • 3753 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.058

  • S = 1.06

  • 3997 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.63 e Å−3

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


Comment top

Recently, many compounds containing a benzofuran moiety have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2011a,b,c), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing (Fig. 2) is stabilized by I···O halogen-bondings between the iodine and the O atom of the sulfonyl group [I1···O2ii = 3.269 (2) Å; C4—11···O2ii = 168.48 (6)°] (Politzer et al., 2007). The crystal packing (Fig. 2) is further stabilized by a weak slipped π···π interaction between the benzene and furan rings of adjacent molecules, with a Cg1···Cg2i distance of 3.701 (3) Å and an interplanar distance of 3.372 (3) Å resulting in a slippage of 1.525 (3) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively, see Fig. 2 for symmetry codes).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 3-cyclohexylsulfonyl-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a,b,c). For a review on halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-chloroperoxybenzoic acid (426 mg, 1.9 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-5-iodo-2,7-dimethyl-1-benzofuran (347 mg, 0.9 mmol) in dichloromethane (35 mL) at 273 K. After being stirred at room temperature for 8h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 441–442 K; Rf = 0.63 (hexane–ethyl acetate, 4:1 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, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methine and methylene, and 1.5Ueq(C) for methyl H atoms.

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 (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 spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the I···O and π···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 2, - z + 1; (ii) - x, - y + 1, - z + 1.]
3-Cyclohexylsulfonyl-5-iodo-2,7-dimethyl-1-benzofuran top
Crystal data top
C16H19IO3SZ = 2
Mr = 418.27F(000) = 416
Triclinic, P1Dx = 1.745 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8643 (2) ÅCell parameters from 8926 reflections
b = 8.4981 (2) Åθ = 2.5–28.4°
c = 14.2323 (3) ŵ = 2.15 mm1
α = 102.512 (1)°T = 173 K
β = 99.846 (1)°Block, colourless
γ = 92.092 (1)°0.24 × 0.16 × 0.14 mm
V = 796.23 (3) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3997 independent reflections
Radiation source: rotating anode3753 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.035
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 1.5°
ϕ and ω scansh = 79
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1111
Tmin = 0.629, Tmax = 0.759l = 1918
15021 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)] = 0.023Hydrogen site location: difference Fourier map
wR(F2) = 0.058H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0291P)2 + 0.2895P]
where P = (Fo2 + 2Fc2)/3
3997 reflections(Δ/σ)max = 0.003
192 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.63 e Å3
Crystal data top
C16H19IO3Sγ = 92.092 (1)°
Mr = 418.27V = 796.23 (3) Å3
Triclinic, P1Z = 2
a = 6.8643 (2) ÅMo Kα radiation
b = 8.4981 (2) ŵ = 2.15 mm1
c = 14.2323 (3) ÅT = 173 K
α = 102.512 (1)°0.24 × 0.16 × 0.14 mm
β = 99.846 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3997 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3753 reflections with I > 2σ(I)
Tmin = 0.629, Tmax = 0.759Rint = 0.035
15021 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.058H-atom parameters constrained
S = 1.06Δρmax = 0.68 e Å3
3997 reflectionsΔρmin = 0.63 e Å3
192 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
I10.227778 (18)0.565947 (15)0.643317 (9)0.02648 (5)
S10.19017 (7)0.68116 (6)0.21668 (4)0.02476 (10)
O10.6820 (2)0.89122 (16)0.38987 (10)0.0237 (3)
O20.0181 (2)0.67742 (19)0.26177 (12)0.0329 (3)
O30.1832 (3)0.76329 (19)0.13777 (12)0.0350 (4)
C10.3897 (3)0.7652 (2)0.30960 (14)0.0224 (4)
C20.4132 (3)0.7461 (2)0.40933 (14)0.0211 (4)
C30.3023 (3)0.6713 (2)0.46236 (14)0.0234 (4)
H30.17610.61630.43360.028*
C40.3852 (3)0.6808 (2)0.55982 (14)0.0229 (4)
C50.5707 (3)0.7612 (2)0.60332 (14)0.0231 (4)
H50.62070.76420.67020.028*
C60.6829 (3)0.8363 (2)0.55159 (15)0.0225 (4)
C70.5962 (3)0.8262 (2)0.45489 (14)0.0211 (4)
C80.5545 (3)0.8523 (2)0.30207 (14)0.0238 (4)
C90.8856 (3)0.9191 (3)0.59487 (16)0.0278 (4)
H9A0.91510.92140.66500.042*
H9B0.88921.03000.58550.042*
H9C0.98460.86000.56230.042*
C100.6225 (3)0.9118 (3)0.22258 (16)0.0311 (4)
H10A0.64781.02970.24210.047*
H10B0.52010.88270.16330.047*
H10C0.74490.86280.20940.047*
C110.2463 (3)0.4764 (2)0.17566 (14)0.0252 (4)
H110.29520.43370.23490.030*
C120.0574 (3)0.3736 (3)0.11981 (17)0.0342 (5)
H12A0.04380.38060.16220.041*
H12B0.00300.41450.06140.041*
C130.1052 (4)0.1980 (3)0.0884 (2)0.0461 (6)
H13A0.14850.15500.14730.055*
H13B0.01600.13240.05000.055*
C140.2662 (4)0.1825 (3)0.0274 (2)0.0446 (6)
H14A0.21800.21510.03460.054*
H14B0.29790.06810.01120.054*
C150.4538 (4)0.2879 (3)0.08190 (18)0.0365 (5)
H15A0.55300.28110.03850.044*
H15B0.51110.24700.13990.044*
C160.4094 (3)0.4643 (3)0.11478 (16)0.0303 (4)
H16A0.53100.52830.15410.036*
H16B0.36720.50960.05670.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02413 (8)0.02921 (8)0.02755 (8)0.00073 (5)0.00534 (5)0.00927 (5)
S10.0237 (2)0.0259 (2)0.0223 (2)0.00194 (18)0.00089 (18)0.00417 (18)
O10.0210 (7)0.0248 (7)0.0242 (7)0.0001 (5)0.0038 (5)0.0039 (5)
O20.0221 (7)0.0389 (9)0.0338 (8)0.0025 (6)0.0019 (6)0.0022 (6)
O30.0392 (9)0.0337 (8)0.0312 (8)0.0025 (7)0.0044 (7)0.0138 (6)
C10.0218 (9)0.0223 (9)0.0211 (9)0.0025 (7)0.0017 (7)0.0024 (7)
C20.0201 (9)0.0189 (8)0.0227 (9)0.0030 (7)0.0030 (7)0.0020 (7)
C30.0197 (9)0.0227 (9)0.0256 (9)0.0006 (7)0.0022 (7)0.0024 (7)
C40.0226 (9)0.0216 (9)0.0254 (9)0.0019 (7)0.0064 (7)0.0054 (7)
C50.0224 (9)0.0237 (9)0.0224 (9)0.0041 (7)0.0017 (7)0.0046 (7)
C60.0204 (9)0.0183 (8)0.0257 (9)0.0030 (7)0.0009 (7)0.0010 (7)
C70.0206 (9)0.0189 (8)0.0239 (9)0.0021 (7)0.0056 (7)0.0039 (7)
C80.0249 (9)0.0223 (9)0.0230 (9)0.0046 (7)0.0025 (7)0.0036 (7)
C90.0202 (9)0.0300 (10)0.0302 (10)0.0015 (8)0.0014 (8)0.0054 (8)
C100.0329 (11)0.0346 (11)0.0277 (10)0.0014 (9)0.0071 (9)0.0100 (8)
C110.0289 (10)0.0245 (9)0.0203 (9)0.0009 (8)0.0019 (8)0.0036 (7)
C120.0302 (11)0.0368 (12)0.0294 (11)0.0073 (9)0.0045 (9)0.0034 (9)
C130.0499 (16)0.0352 (13)0.0436 (14)0.0134 (11)0.0089 (12)0.0092 (10)
C140.0479 (15)0.0363 (13)0.0398 (13)0.0014 (11)0.0066 (11)0.0106 (10)
C150.0369 (13)0.0331 (12)0.0353 (12)0.0053 (9)0.0057 (10)0.0009 (9)
C160.0304 (11)0.0312 (11)0.0286 (10)0.0011 (8)0.0068 (9)0.0047 (8)
Geometric parameters (Å, º) top
I1—C42.097 (2)C9—H9C0.9800
I1—O2i3.2688 (17)C10—H10A0.9800
S1—O21.4401 (17)C10—H10B0.9800
S1—O31.4403 (16)C10—H10C0.9800
S1—C11.742 (2)C11—C161.522 (3)
S1—C111.790 (2)C11—C121.530 (3)
O1—C81.365 (2)C11—H111.0000
O1—C71.376 (2)C12—C131.527 (3)
C1—C81.361 (3)C12—H12A0.9900
C1—C21.446 (3)C12—H12B0.9900
C2—C31.386 (3)C13—C141.510 (4)
C2—C71.389 (3)C13—H13A0.9900
C3—C41.390 (3)C13—H13B0.9900
C3—H30.9500C14—C151.528 (3)
C4—C51.398 (3)C14—H14A0.9900
C5—C61.380 (3)C14—H14B0.9900
C5—H50.9500C15—C161.529 (3)
C6—C71.386 (3)C15—H15A0.9900
C6—C91.503 (3)C15—H15B0.9900
C8—C101.472 (3)C16—H16A0.9900
C9—H9A0.9800C16—H16B0.9900
C9—H9B0.9800
C4—I1—O2i168.48 (6)H10A—C10—H10B109.5
O2—S1—O3118.27 (10)C8—C10—H10C109.5
O2—S1—C1107.00 (9)H10A—C10—H10C109.5
O3—S1—C1109.53 (10)H10B—C10—H10C109.5
O2—S1—C11107.41 (10)C16—C11—C12111.79 (17)
O3—S1—C11109.40 (10)C16—C11—S1111.94 (14)
C1—S1—C11104.32 (9)C12—C11—S1109.81 (15)
C8—O1—C7107.13 (15)C16—C11—H11107.7
C8—C1—C2107.46 (17)C12—C11—H11107.7
C8—C1—S1127.49 (16)S1—C11—H11107.7
C2—C1—S1124.98 (15)C13—C12—C11109.4 (2)
C3—C2—C7119.59 (18)C13—C12—H12A109.8
C3—C2—C1135.79 (18)C11—C12—H12A109.8
C7—C2—C1104.61 (17)C13—C12—H12B109.8
C2—C3—C4116.60 (18)C11—C12—H12B109.8
C2—C3—H3121.7H12A—C12—H12B108.2
C4—C3—H3121.7C14—C13—C12111.6 (2)
C3—C4—C5122.42 (19)C14—C13—H13A109.3
C3—C4—I1118.52 (14)C12—C13—H13A109.3
C5—C4—I1119.05 (14)C14—C13—H13B109.3
C6—C5—C4121.71 (18)C12—C13—H13B109.3
C6—C5—H5119.1H13A—C13—H13B108.0
C4—C5—H5119.1C13—C14—C15111.3 (2)
C5—C6—C7114.71 (17)C13—C14—H14A109.4
C5—C6—C9123.24 (19)C15—C14—H14A109.4
C7—C6—C9122.03 (19)C13—C14—H14B109.4
O1—C7—C6124.57 (17)C15—C14—H14B109.4
O1—C7—C2110.47 (16)H14A—C14—H14B108.0
C6—C7—C2124.95 (19)C14—C15—C16111.3 (2)
C1—C8—O1110.33 (17)C14—C15—H15A109.4
C1—C8—C10134.78 (19)C16—C15—H15A109.4
O1—C8—C10114.89 (18)C14—C15—H15B109.4
C6—C9—H9A109.5C16—C15—H15B109.4
C6—C9—H9B109.5H15A—C15—H15B108.0
H9A—C9—H9B109.5C11—C16—C15110.27 (19)
C6—C9—H9C109.5C11—C16—H16A109.6
H9A—C9—H9C109.5C15—C16—H16A109.6
H9B—C9—H9C109.5C11—C16—H16B109.6
C8—C10—H10A109.5C15—C16—H16B109.6
C8—C10—H10B109.5H16A—C16—H16B108.1
O2—S1—C1—C8150.57 (18)C9—C6—C7—C2177.36 (18)
O3—S1—C1—C821.2 (2)C3—C2—C7—O1179.81 (16)
C11—S1—C1—C895.78 (19)C1—C2—C7—O10.2 (2)
O2—S1—C1—C232.94 (19)C3—C2—C7—C61.2 (3)
O3—S1—C1—C2162.28 (16)C1—C2—C7—C6178.46 (18)
C11—S1—C1—C280.70 (18)C2—C1—C8—O10.2 (2)
C8—C1—C2—C3179.5 (2)S1—C1—C8—O1177.21 (14)
S1—C1—C2—C32.4 (3)C2—C1—C8—C10179.9 (2)
C8—C1—C2—C70.0 (2)S1—C1—C8—C102.9 (4)
S1—C1—C2—C7177.11 (14)C7—O1—C8—C10.3 (2)
C7—C2—C3—C40.5 (3)C7—O1—C8—C10179.77 (16)
C1—C2—C3—C4179.0 (2)O2—S1—C11—C16172.45 (14)
C2—C3—C4—C50.0 (3)O3—S1—C11—C1642.91 (17)
C2—C3—C4—I1178.70 (13)C1—S1—C11—C1674.20 (16)
O2i—I1—C4—C354.4 (4)O2—S1—C11—C1247.67 (17)
O2i—I1—C4—C5124.3 (3)O3—S1—C11—C1281.87 (17)
C3—C4—C5—C60.0 (3)C1—S1—C11—C12161.02 (15)
I1—C4—C5—C6178.69 (14)C16—C11—C12—C1357.2 (3)
C4—C5—C6—C70.5 (3)S1—C11—C12—C13177.91 (17)
C4—C5—C6—C9177.95 (18)C11—C12—C13—C1456.7 (3)
C8—O1—C7—C6178.33 (18)C12—C13—C14—C1556.3 (3)
C8—O1—C7—C20.3 (2)C13—C14—C15—C1655.2 (3)
C5—C6—C7—O1179.56 (17)C12—C11—C16—C1556.8 (2)
C9—C6—C7—O11.1 (3)S1—C11—C16—C15179.57 (15)
C5—C6—C7—C21.1 (3)C14—C15—C16—C1155.0 (3)
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC16H19IO3S
Mr418.27
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.8643 (2), 8.4981 (2), 14.2323 (3)
α, β, γ (°)102.512 (1), 99.846 (1), 92.092 (1)
V3)796.23 (3)
Z2
Radiation typeMo Kα
µ (mm1)2.15
Crystal size (mm)0.24 × 0.16 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.629, 0.759
No. of measured, independent and
observed [I > 2σ(I)] reflections
15021, 3997, 3753
Rint0.035
(sin θ/λ)max1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.058, 1.06
No. of reflections3997
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.63

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

 

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