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

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ISSN: 2056-9890

2-(4-Fluoro­phen­yl)-5-iodo-3-phenyl­sulfinyl-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 19 March 2012; accepted 26 March 2012; online 27 March 2012)

In the title compound, C20H12FIO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.014 (1) Å] of the benzofuran fragment and the pendant 4-fluoro­phenyl and phenyl rings are 8.0 (1) and 86.06 (6)°, respectively. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds. The crystal structure also exhibits weak ππ inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.547 (2) Å, inter­planar distance = 3.397 (2) Å and slippage = 1.021 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o498.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.]).

[Scheme 1]

Experimental

Crystal data
  • C20H12FIO2S

  • Mr = 462.26

  • Triclinic, [P \overline 1]

  • a = 8.1771 (2) Å

  • b = 9.8877 (2) Å

  • c = 11.8423 (3) Å

  • α = 103.108 (1)°

  • β = 90.872 (1)°

  • γ = 111.546 (1)°

  • V = 862.23 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.00 mm−1

  • T = 173 K

  • 0.27 × 0.26 × 0.12 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 = 0.516, Tmax = 0.746

  • 15186 measured reflections

  • 3974 independent reflections

  • 3696 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.024

  • wR(F2) = 0.060

  • S = 1.07

  • 3974 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.75 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C19—H19⋯O2i 0.95 2.38 3.297 (3) 163
Symmetry code: (i) x+1, y, z.

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

As a part of our ongoing study of 2-(4-fluorophenyl)-5-halo-3-phenylsulfinyl-1-benzofuran derivatives containing 5-chloro (Choi et al., 2011) and 5-bromo (Seo et al., 2011) substituents, 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 0.014 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 8.0 (1)° and 86.06 (6)°, respectively. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is further stabilized by weak ππ interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2ii distance of 3.547 (2) Å and an interplanar distance of 3.397 (2) Å resulting in a slippage of 1.021 (2) Å (Cg1 and Cg2are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011); Seo et al. (2011).

Experimental top

77% 3-Chloroperoxybenzoic acid (179 mg, 0.8 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-phenylsulfanyl-1-benzofuran (312 mg, 0.7 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 4h, 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 52%, m.p. 435–436 K; Rf = 0.49 (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 ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å (C-aromatic). Uiso(H) =1.2Ueq(C-aromatic).

Structure description top

As a part of our ongoing study of 2-(4-fluorophenyl)-5-halo-3-phenylsulfinyl-1-benzofuran derivatives containing 5-chloro (Choi et al., 2011) and 5-bromo (Seo et al., 2011) substituents, 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 0.014 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 8.0 (1)° and 86.06 (6)°, respectively. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is further stabilized by weak ππ interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2ii distance of 3.547 (2) Å and an interplanar distance of 3.397 (2) Å resulting in a slippage of 1.021 (2) Å (Cg1 and Cg2are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively).

For background information and the crystal structures of related compounds, see: Choi et al. (2011); Seo et al. (2011).

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.
[Figure 2] Fig. 2. A view of the C—H···O and ππ interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [ Symmetry codes: (i) x + 1, y, z; (ii) - x, - y + 1, -z + 1; (iii) - x, - y + 1, - z + 1.]
2-(4-Fluorophenyl)-5-iodo-3-phenylsulfinyl-1-benzofuran top
Crystal data top
C20H12FIO2SZ = 2
Mr = 462.26F(000) = 452
Triclinic, P1Dx = 1.780 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1771 (2) ÅCell parameters from 9967 reflections
b = 9.8877 (2) Åθ = 2.5–27.5°
c = 11.8423 (3) ŵ = 2.00 mm1
α = 103.108 (1)°T = 173 K
β = 90.872 (1)°Block, colourless
γ = 111.546 (1)°0.27 × 0.26 × 0.12 mm
V = 862.23 (4) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3974 independent reflections
Radiation source: rotating anode3696 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.026
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.8°
φ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1212
Tmin = 0.516, Tmax = 0.746l = 1515
15186 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)] = 0.024Hydrogen site location: difference Fourier map
wR(F2) = 0.060H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0266P)2 + 0.5718P]
where P = (Fo2 + 2Fc2)/3
3974 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.75 e Å3
Crystal data top
C20H12FIO2Sγ = 111.546 (1)°
Mr = 462.26V = 862.23 (4) Å3
Triclinic, P1Z = 2
a = 8.1771 (2) ÅMo Kα radiation
b = 9.8877 (2) ŵ = 2.00 mm1
c = 11.8423 (3) ÅT = 173 K
α = 103.108 (1)°0.27 × 0.26 × 0.12 mm
β = 90.872 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3974 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3696 reflections with I > 2σ(I)
Tmin = 0.516, Tmax = 0.746Rint = 0.026
15186 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.07Δρmax = 0.50 e Å3
3974 reflectionsΔρmin = 0.75 e Å3
226 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
I10.02004 (2)0.736536 (19)0.939462 (12)0.04406 (7)
S10.04558 (6)0.18031 (5)0.55834 (4)0.02240 (10)
F10.4764 (2)0.12714 (16)0.06431 (11)0.0421 (3)
O10.29632 (18)0.56238 (13)0.46924 (11)0.0224 (3)
O20.10716 (18)0.17443 (17)0.62692 (14)0.0317 (3)
C10.1437 (2)0.36524 (19)0.54025 (15)0.0203 (3)
C20.1408 (2)0.4983 (2)0.61933 (15)0.0212 (3)
C30.0716 (3)0.5302 (2)0.72497 (16)0.0252 (4)
H30.00360.45280.75980.030*
C40.1067 (3)0.6796 (2)0.77636 (17)0.0283 (4)
C50.2028 (3)0.7961 (2)0.72598 (18)0.0296 (4)
H50.22270.89710.76440.035*
C60.2688 (3)0.7648 (2)0.62058 (17)0.0267 (4)
H60.33290.84190.58430.032*
C70.2368 (2)0.6155 (2)0.57083 (15)0.0217 (3)
C80.2380 (2)0.40854 (19)0.45144 (15)0.0203 (3)
C90.2959 (2)0.3331 (2)0.34844 (15)0.0212 (3)
C100.2368 (3)0.1764 (2)0.31272 (17)0.0278 (4)
H100.15430.11690.35490.033*
C110.2971 (3)0.1071 (2)0.21679 (18)0.0317 (4)
H110.25720.00070.19290.038*
C120.4154 (3)0.1950 (2)0.15691 (16)0.0289 (4)
C130.4753 (3)0.3489 (2)0.18758 (17)0.0283 (4)
H130.55650.40680.14390.034*
C140.4147 (3)0.4179 (2)0.28375 (16)0.0248 (4)
H140.45450.52440.30590.030*
C150.2209 (2)0.1910 (2)0.65768 (16)0.0226 (4)
C160.2111 (3)0.2277 (3)0.77601 (18)0.0346 (5)
H160.11150.24580.80530.042*
C170.3483 (4)0.2380 (3)0.8519 (2)0.0433 (6)
H170.34280.26300.93370.052*
C180.4935 (3)0.2120 (3)0.8089 (2)0.0386 (5)
H180.58830.22110.86130.046*
C190.5009 (3)0.1729 (2)0.6898 (2)0.0330 (4)
H190.60010.15410.66050.040*
C200.3635 (3)0.1612 (2)0.61308 (18)0.0275 (4)
H200.36700.13310.53120.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04049 (10)0.06314 (12)0.02678 (8)0.02727 (8)0.00553 (6)0.00508 (7)
S10.0202 (2)0.0189 (2)0.0272 (2)0.00549 (17)0.00357 (17)0.00708 (16)
F10.0526 (9)0.0506 (8)0.0284 (6)0.0319 (7)0.0107 (6)0.0008 (6)
O10.0269 (7)0.0166 (6)0.0225 (6)0.0077 (5)0.0037 (5)0.0036 (5)
O20.0197 (7)0.0361 (8)0.0429 (8)0.0101 (6)0.0104 (6)0.0171 (6)
C10.0192 (8)0.0192 (8)0.0230 (8)0.0079 (7)0.0014 (7)0.0050 (6)
C20.0194 (9)0.0219 (8)0.0220 (8)0.0090 (7)0.0003 (7)0.0030 (7)
C30.0221 (9)0.0305 (10)0.0235 (9)0.0116 (8)0.0023 (7)0.0046 (7)
C40.0250 (10)0.0359 (10)0.0230 (9)0.0159 (9)0.0008 (7)0.0020 (7)
C50.0302 (11)0.0250 (9)0.0311 (10)0.0141 (8)0.0030 (8)0.0033 (7)
C60.0281 (10)0.0208 (9)0.0300 (9)0.0099 (8)0.0000 (8)0.0032 (7)
C70.0218 (9)0.0223 (8)0.0213 (8)0.0101 (7)0.0009 (7)0.0029 (7)
C80.0201 (9)0.0167 (8)0.0232 (8)0.0068 (7)0.0004 (7)0.0038 (6)
C90.0216 (9)0.0226 (8)0.0194 (8)0.0097 (7)0.0006 (7)0.0035 (7)
C100.0340 (11)0.0228 (9)0.0260 (9)0.0106 (8)0.0054 (8)0.0049 (7)
C110.0414 (12)0.0258 (9)0.0281 (10)0.0166 (9)0.0011 (9)0.0008 (8)
C120.0311 (11)0.0391 (11)0.0200 (8)0.0217 (9)0.0011 (8)0.0001 (8)
C130.0260 (10)0.0367 (10)0.0231 (9)0.0131 (9)0.0042 (7)0.0069 (8)
C140.0245 (9)0.0236 (9)0.0247 (9)0.0082 (8)0.0019 (7)0.0044 (7)
C150.0209 (9)0.0199 (8)0.0281 (9)0.0074 (7)0.0039 (7)0.0089 (7)
C160.0363 (12)0.0484 (13)0.0304 (10)0.0265 (11)0.0095 (9)0.0134 (9)
C170.0509 (15)0.0615 (15)0.0276 (10)0.0328 (13)0.0023 (10)0.0115 (10)
C180.0343 (12)0.0424 (12)0.0439 (13)0.0185 (10)0.0033 (10)0.0139 (10)
C190.0247 (10)0.0329 (11)0.0477 (12)0.0148 (9)0.0083 (9)0.0157 (9)
C200.0280 (10)0.0255 (9)0.0328 (10)0.0125 (8)0.0089 (8)0.0103 (8)
Geometric parameters (Å, º) top
I1—C42.096 (2)C9—C101.399 (3)
S1—O21.4905 (15)C10—C111.384 (3)
S1—C11.7716 (18)C10—H100.9500
S1—C151.7978 (19)C11—C121.371 (3)
F1—C121.353 (2)C11—H110.9500
O1—C71.371 (2)C12—C131.372 (3)
O1—C81.380 (2)C13—C141.386 (3)
C1—C81.368 (3)C13—H130.9500
C1—C21.440 (2)C14—H140.9500
C2—C71.392 (3)C15—C161.377 (3)
C2—C31.400 (3)C15—C201.388 (3)
C3—C41.382 (3)C16—C171.386 (3)
C3—H30.9500C16—H160.9500
C4—C51.401 (3)C17—C181.385 (4)
C5—C61.383 (3)C17—H170.9500
C5—H50.9500C18—C191.384 (3)
C6—C71.383 (3)C18—H180.9500
C6—H60.9500C19—C201.388 (3)
C8—C91.460 (2)C19—H190.9500
C9—C141.397 (3)C20—H200.9500
O2—S1—C1107.18 (8)C11—C10—H10119.6
O2—S1—C15106.52 (9)C9—C10—H10119.6
C1—S1—C1597.14 (8)C12—C11—C10118.61 (19)
C7—O1—C8106.99 (14)C12—C11—H11120.7
C8—C1—C2107.66 (15)C10—C11—H11120.7
C8—C1—S1126.91 (14)F1—C12—C11118.54 (19)
C2—C1—S1125.42 (14)F1—C12—C13118.78 (19)
C7—C2—C3119.34 (17)C11—C12—C13122.67 (18)
C7—C2—C1104.82 (15)C12—C13—C14118.54 (19)
C3—C2—C1135.82 (17)C12—C13—H13120.7
C4—C3—C2116.96 (18)C14—C13—H13120.7
C4—C3—H3121.5C13—C14—C9120.84 (18)
C2—C3—H3121.5C13—C14—H14119.6
C3—C4—C5122.95 (18)C9—C14—H14119.6
C3—C4—I1118.98 (15)C16—C15—C20121.34 (18)
C5—C4—I1118.05 (14)C16—C15—S1119.61 (15)
C6—C5—C4120.26 (18)C20—C15—S1119.05 (15)
C6—C5—H5119.9C15—C16—C17119.1 (2)
C4—C5—H5119.9C15—C16—H16120.4
C7—C6—C5116.56 (18)C17—C16—H16120.4
C7—C6—H6121.7C18—C17—C16120.3 (2)
C5—C6—H6121.7C18—C17—H17119.9
O1—C7—C6125.34 (17)C16—C17—H17119.9
O1—C7—C2110.74 (15)C19—C18—C17120.2 (2)
C6—C7—C2123.92 (17)C19—C18—H18119.9
C1—C8—O1109.79 (15)C17—C18—H18119.9
C1—C8—C9135.62 (16)C18—C19—C20120.0 (2)
O1—C8—C9114.52 (15)C18—C19—H19120.0
C14—C9—C10118.46 (17)C20—C19—H19120.0
C14—C9—C8119.83 (16)C19—C20—C15119.06 (19)
C10—C9—C8121.71 (17)C19—C20—H20120.5
C11—C10—C9120.86 (19)C15—C20—H20120.5
O2—S1—C1—C8153.19 (16)C7—O1—C8—C9177.64 (15)
C15—S1—C1—C897.02 (18)C1—C8—C9—C14170.7 (2)
O2—S1—C1—C228.24 (18)O1—C8—C9—C145.9 (2)
C15—S1—C1—C281.55 (17)C1—C8—C9—C108.5 (3)
C8—C1—C2—C70.1 (2)O1—C8—C9—C10174.81 (17)
S1—C1—C2—C7178.71 (13)C14—C9—C10—C111.2 (3)
C8—C1—C2—C3178.5 (2)C8—C9—C10—C11178.14 (18)
S1—C1—C2—C30.3 (3)C9—C10—C11—C120.3 (3)
C7—C2—C3—C41.2 (3)C10—C11—C12—F1178.92 (18)
C1—C2—C3—C4177.1 (2)C10—C11—C12—C130.6 (3)
C2—C3—C4—C51.6 (3)F1—C12—C13—C14178.90 (18)
C2—C3—C4—I1176.41 (13)C11—C12—C13—C140.6 (3)
C3—C4—C5—C60.5 (3)C12—C13—C14—C90.3 (3)
I1—C4—C5—C6177.47 (15)C10—C9—C14—C131.1 (3)
C4—C5—C6—C70.9 (3)C8—C9—C14—C13178.18 (17)
C8—O1—C7—C6179.10 (18)O2—S1—C15—C1615.33 (19)
C8—O1—C7—C20.1 (2)C1—S1—C15—C1695.01 (17)
C5—C6—C7—O1177.58 (18)O2—S1—C15—C20164.42 (15)
C5—C6—C7—C21.3 (3)C1—S1—C15—C2085.24 (16)
C3—C2—C7—O1178.77 (16)C20—C15—C16—C171.3 (3)
C1—C2—C7—O10.0 (2)S1—C15—C16—C17178.96 (18)
C3—C2—C7—C60.3 (3)C15—C16—C17—C180.2 (4)
C1—C2—C7—C6179.03 (18)C16—C17—C18—C191.2 (4)
C2—C1—C8—O10.1 (2)C17—C18—C19—C200.7 (3)
S1—C1—C8—O1178.64 (13)C18—C19—C20—C150.8 (3)
C2—C1—C8—C9176.9 (2)C16—C15—C20—C191.8 (3)
S1—C1—C8—C91.9 (3)S1—C15—C20—C19178.46 (15)
C7—O1—C8—C10.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O2i0.952.383.297 (3)163
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC20H12FIO2S
Mr462.26
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.1771 (2), 9.8877 (2), 11.8423 (3)
α, β, γ (°)103.108 (1), 90.872 (1), 111.546 (1)
V3)862.23 (4)
Z2
Radiation typeMo Kα
µ (mm1)2.00
Crystal size (mm)0.27 × 0.26 × 0.12
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.516, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
15186, 3974, 3696
Rint0.026
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.060, 1.07
No. of reflections3974
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.75

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O2i0.952.383.297 (3)163.4
Symmetry code: (i) x+1, y, z.
 

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., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o498.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationSeo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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