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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2468.
Published online 2010 August 28. doi:  10.1107/S1600536810033787
PMCID: PMC3007899

1-[4-(3,5-Difluoro­benz­yloxy)-2-hy­droxy­phen­yl]ethanone

Abstract

The title compound, C15H12F2O3, has been obtained by the reaction of 2,4-dihy­droxy­lacetonephenone, potassium carbonate and 3,5-difluoro­benzyl bromide. The hy­droxy group is involved in an intra­molecular O—H(...)O hydrogen bond in each of the two independent mol­ecules in the asymmetric unit. The dihedral angle between the aromatic rings is 0.5 (2)° in one molecule and 1.9 (2)° in the other. In the crystal, weak C—H(...)O inter­actions link the mol­ecules into tetra­meric units aligned perpendicular to b.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934 [triangle]). For a related structure, see: Ma et al. (2010 [triangle]).

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Object name is e-66-o2468-scheme1.jpg

Experimental

Crystal data

  • C15H12F2O3
  • M r = 278.25
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2468-efi1.jpg
  • a = 7.4220 (8) Å
  • b = 13.0329 (14) Å
  • c = 14.1171 (16) Å
  • α = 83.921 (2)°
  • β = 77.913 (1)°
  • γ = 76.501 (1)°
  • V = 1296.1 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 298 K
  • 0.40 × 0.32 × 0.28 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.955, T max = 0.968
  • 6817 measured reflections
  • 4491 independent reflections
  • 2244 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.072
  • wR(F 2) = 0.231
  • S = 0.96
  • 4491 reflections
  • 363 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033787/bv2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033787/bv2156Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We would like to acknowledge funding support from the National Natural Science Foundation of China (grant No. 30971882) and the Program of Natural Science Basic Research in Shaanxi (No. 2009JM3010).

supplementary crystallographic information

Comment

The Williamson reaction is a very useful transformation in organic synthesis since the products are of value in both industrial and academic applications. It usually involves the employment of an alkali-metal salt of the hydroxy compound and an alkylhalide (Dermer, 1934).

In this paper, we present the title compound, (I), which was synthesized by the reaction of 2,4-dihydroxylacetonephenone, potassium carbonate and 3,5-difluorobenzyl bromide. In (I) (Fig. 1), the bond lengths and angles are normal and the dihedral angle between the aromatic rings is 0.51 (4)°. In addition to the intramolecular O—H···O hydrogen bonds, there are weak C—H···O interactions which link the molecules into tetrameric units aligned perpendicular to b (see Fig. 2).

Experimental

2,4-Dihydroxylacetonephenone (4 mmol), potassium carbonate (8 mmol), 3,5-difluorobenzyl bromide (4 mmol), and 40 ml acetone were mixed in 100 ml flask. After 3 h stirring at 331 K, the crude product was obtained. The crystals were obtained by recrystallization from n-hexane/ethyl acetate.

Refinement

The positions of all H atoms were fixed geometrically and distance to H atoms were set by the program, with C—H distance in the range 0.93–0.97 Å and O—H distance of 0.82 Å.

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. Both the C—H···O interaction and the intramolecular hydrogen bonds are shown by dashed lines.
Fig. 2.
The packing viewed down the b axis showing the tetrameric units linked by C—H···O interactions. Both these interactions and the intramolecular hydrogen bonds are shown by dashed lines.

Crystal data

C15H12F2O3Z = 4
Mr = 278.25F(000) = 576
Triclinic, P1Dx = 1.426 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4220 (8) ÅCell parameters from 1571 reflections
b = 13.0329 (14) Åθ = 2.4–23.0°
c = 14.1171 (16) ŵ = 0.12 mm1
α = 83.921 (2)°T = 298 K
β = 77.913 (1)°Triclinic, colorless
γ = 76.501 (1)°0.40 × 0.32 × 0.28 mm
V = 1296.1 (2) Å3

Data collection

Siemens SMART CCD area-detector diffractometer4491 independent reflections
Radiation source: fine-focus sealed tube2244 reflections with I > 2σ(I)
graphiteRint = 0.036
ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.955, Tmax = 0.968k = −13→15
6817 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.231H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.1234P)2] where P = (Fo2 + 2Fc2)/3
4491 reflections(Δ/σ)max < 0.001
363 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
F11.1302 (5)−0.2012 (2)−0.40710 (17)0.1012 (10)
F21.0857 (4)0.1549 (2)−0.36867 (17)0.0938 (10)
O10.3966 (4)−0.0294 (2)0.39116 (18)0.0685 (9)
O20.5359 (4)−0.1407 (2)0.24593 (18)0.0660 (9)
H20.4839−0.12780.30200.099*
O30.7935 (4)0.0311 (2)−0.04745 (16)0.0550 (8)
C10.3850 (7)0.1531 (3)0.3919 (3)0.0710 (13)
H1A0.33600.14140.45970.106*
H1B0.29130.20230.36260.106*
H1C0.49580.18150.38440.106*
C20.4350 (6)0.0503 (3)0.3436 (3)0.0537 (10)
C30.5232 (5)0.0463 (3)0.2413 (2)0.0429 (9)
C40.5740 (5)−0.0511 (3)0.1963 (2)0.0450 (9)
C50.6623 (5)−0.0580 (3)0.1002 (2)0.0457 (9)
H5A0.6932−0.12270.07190.055*
C60.7044 (5)0.0296 (3)0.0468 (2)0.0425 (9)
C70.6561 (5)0.1271 (3)0.0888 (2)0.0499 (10)
H70.68320.18710.05220.060*
C80.5688 (5)0.1336 (3)0.1839 (2)0.0486 (10)
H80.53870.19870.21130.058*
C90.8450 (6)−0.0657 (3)−0.0942 (2)0.0511 (10)
H9A0.7336−0.0936−0.09150.061*
H9B0.9319−0.1171−0.06100.061*
C100.9362 (5)−0.0474 (3)−0.1973 (2)0.0453 (9)
C110.9919 (6)−0.1327 (3)−0.2559 (3)0.0585 (11)
H110.9724−0.1990−0.23090.070*
C121.0756 (6)−0.1181 (4)−0.3505 (3)0.0630 (12)
C131.1114 (6)−0.0235 (4)−0.3913 (3)0.0592 (11)
H131.1714−0.0155−0.45560.071*
C141.0529 (6)0.0592 (3)−0.3312 (3)0.0582 (11)
C150.9681 (6)0.0493 (3)−0.2359 (3)0.0543 (10)
H150.93270.1073−0.19780.065*
F3−0.1980 (4)0.6542 (2)0.85834 (18)0.1013 (10)
F4−0.0009 (4)0.2932 (2)0.93069 (17)0.0972 (10)
O40.6255 (5)0.4794 (2)0.11718 (18)0.0730 (9)
O50.5718 (4)0.3646 (2)0.27167 (18)0.0697 (9)
H50.61430.37930.21470.104*
O60.1814 (4)0.5295 (2)0.55010 (16)0.0569 (8)
C160.4955 (7)0.6621 (4)0.1001 (3)0.0734 (14)
H16A0.56100.65230.03430.110*
H16B0.54330.71210.12770.110*
H16C0.36300.68830.10100.110*
C170.5250 (6)0.5590 (3)0.1580 (3)0.0551 (11)
C180.4401 (5)0.5514 (3)0.2605 (2)0.0426 (9)
C190.4657 (6)0.4531 (3)0.3139 (2)0.0487 (10)
C200.3820 (5)0.4430 (3)0.4103 (2)0.0476 (10)
H200.39950.37740.44410.057*
C210.2719 (5)0.5314 (3)0.4563 (2)0.0425 (9)
C220.2473 (6)0.6292 (3)0.4062 (2)0.0519 (10)
H220.17480.68860.43770.062*
C230.3298 (5)0.6385 (3)0.3104 (2)0.0501 (10)
H230.31190.70470.27750.060*
C240.2003 (6)0.4312 (3)0.6062 (2)0.0500 (10)
H24A0.33250.40140.60700.060*
H24B0.15130.38180.57720.060*
C250.0940 (5)0.4486 (3)0.7071 (2)0.0452 (9)
C26−0.0051 (6)0.5473 (3)0.7369 (3)0.0533 (10)
H26−0.00670.60630.69360.064*
C27−0.1003 (6)0.5569 (3)0.8303 (3)0.0602 (12)
C28−0.1032 (6)0.4739 (3)0.8982 (3)0.0573 (11)
H28−0.16890.48210.96160.069*
C29−0.0026 (6)0.3781 (3)0.8659 (3)0.0575 (11)
C300.0951 (6)0.3632 (3)0.7736 (3)0.0564 (11)
H300.16190.29620.75560.068*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.142 (3)0.099 (2)0.0589 (15)−0.0326 (19)0.0144 (17)−0.0386 (15)
F20.127 (3)0.0745 (19)0.0608 (16)−0.0203 (17)0.0172 (16)0.0074 (14)
O10.083 (2)0.070 (2)0.0420 (15)−0.0189 (17)0.0142 (15)−0.0045 (14)
O20.090 (2)0.0521 (18)0.0466 (15)−0.0224 (16)0.0132 (15)0.0016 (13)
O30.0694 (19)0.0644 (18)0.0293 (13)−0.0207 (15)0.0041 (13)−0.0077 (12)
C10.086 (3)0.074 (3)0.049 (2)−0.019 (3)0.007 (2)−0.022 (2)
C20.056 (3)0.062 (3)0.039 (2)−0.015 (2)0.0019 (19)−0.005 (2)
C30.043 (2)0.051 (2)0.0352 (19)−0.0133 (18)−0.0034 (17)−0.0077 (17)
C40.043 (2)0.052 (2)0.037 (2)−0.0114 (18)−0.0008 (17)0.0014 (18)
C50.047 (2)0.051 (2)0.036 (2)−0.0091 (18)−0.0026 (18)−0.0065 (18)
C60.041 (2)0.054 (2)0.0288 (18)−0.0096 (18)0.0004 (16)−0.0030 (17)
C70.064 (3)0.047 (2)0.037 (2)−0.018 (2)−0.0015 (19)0.0012 (18)
C80.053 (2)0.046 (2)0.043 (2)−0.0099 (18)−0.0010 (19)−0.0058 (17)
C90.057 (3)0.061 (3)0.0338 (19)−0.015 (2)−0.0017 (18)−0.0044 (19)
C100.041 (2)0.061 (3)0.0335 (19)−0.0099 (19)−0.0082 (17)−0.0045 (18)
C110.066 (3)0.069 (3)0.041 (2)−0.023 (2)0.002 (2)−0.013 (2)
C120.067 (3)0.077 (3)0.048 (2)−0.015 (2)−0.005 (2)−0.028 (2)
C130.054 (3)0.085 (3)0.034 (2)−0.011 (2)0.0031 (19)−0.011 (2)
C140.058 (3)0.067 (3)0.041 (2)−0.010 (2)−0.001 (2)0.009 (2)
C150.054 (3)0.065 (3)0.038 (2)−0.006 (2)−0.0040 (19)−0.0027 (19)
F30.135 (3)0.0683 (19)0.0704 (17)−0.0089 (17)0.0385 (17)−0.0170 (14)
F40.118 (2)0.0870 (19)0.0553 (15)0.0010 (16)0.0135 (15)0.0235 (14)
O40.091 (2)0.078 (2)0.0414 (16)−0.0216 (18)0.0155 (16)−0.0122 (15)
O50.094 (2)0.0533 (18)0.0471 (16)−0.0092 (16)0.0153 (16)−0.0126 (14)
O60.0694 (19)0.0613 (18)0.0321 (13)−0.0113 (14)0.0052 (13)−0.0041 (13)
C160.090 (4)0.081 (3)0.044 (2)−0.025 (3)−0.002 (2)0.010 (2)
C170.059 (3)0.068 (3)0.040 (2)−0.023 (2)−0.002 (2)−0.005 (2)
C180.047 (2)0.050 (2)0.0326 (18)−0.0149 (18)−0.0043 (17)−0.0038 (17)
C190.057 (3)0.052 (2)0.037 (2)−0.018 (2)−0.0007 (18)−0.0101 (19)
C200.059 (3)0.050 (2)0.0332 (19)−0.018 (2)−0.0017 (18)−0.0015 (17)
C210.048 (2)0.052 (2)0.0277 (18)−0.0162 (19)−0.0014 (16)−0.0039 (17)
C220.057 (3)0.053 (3)0.041 (2)−0.0044 (19)−0.0054 (19)−0.0074 (18)
C230.057 (3)0.049 (2)0.041 (2)−0.0092 (19)−0.0043 (19)−0.0008 (18)
C240.057 (3)0.057 (3)0.035 (2)−0.016 (2)−0.0040 (18)−0.0013 (18)
C250.040 (2)0.063 (3)0.0336 (19)−0.0141 (19)−0.0031 (16)−0.0079 (18)
C260.064 (3)0.055 (3)0.038 (2)−0.017 (2)0.002 (2)0.0002 (19)
C270.070 (3)0.051 (3)0.050 (2)−0.011 (2)0.010 (2)−0.010 (2)
C280.060 (3)0.076 (3)0.032 (2)−0.015 (2)0.0041 (19)−0.008 (2)
C290.065 (3)0.063 (3)0.038 (2)−0.012 (2)−0.005 (2)0.012 (2)
C300.060 (3)0.060 (3)0.042 (2)−0.006 (2)−0.004 (2)0.000 (2)

Geometric parameters (Å, °)

F1—C121.349 (4)F3—C271.358 (5)
F2—C141.357 (4)F4—C291.358 (4)
O1—C21.234 (4)O4—C171.245 (5)
O2—C41.353 (4)O5—C191.352 (4)
O2—H20.8207O5—H50.8205
O3—C61.356 (4)O6—C211.354 (4)
O3—C91.421 (4)O6—C241.426 (4)
C1—C21.501 (5)C16—C171.491 (5)
C1—H1A0.9600C16—H16A0.9600
C1—H1B0.9600C16—H16B0.9600
C1—H1C0.9600C16—H16C0.9600
C2—C31.456 (5)C17—C181.456 (5)
C3—C81.391 (5)C18—C231.396 (5)
C3—C41.416 (5)C18—C191.410 (5)
C4—C51.380 (4)C19—C201.379 (5)
C5—C61.362 (5)C20—C211.383 (5)
C5—H5A0.9300C20—H200.9300
C6—C71.397 (5)C21—C221.383 (5)
C7—C81.366 (4)C22—C231.369 (5)
C7—H70.9300C22—H220.9300
C8—H80.9300C23—H230.9300
C9—C101.492 (5)C24—C251.490 (4)
C9—H9A0.9700C24—H24A0.9700
C9—H9B0.9700C24—H24B0.9700
C10—C151.371 (5)C25—C301.376 (5)
C10—C111.387 (5)C25—C261.384 (5)
C11—C121.364 (5)C26—C271.362 (5)
C11—H110.9300C26—H260.9300
C12—C131.364 (5)C27—C281.368 (5)
C13—C141.375 (5)C28—C291.367 (6)
C13—H130.9300C28—H280.9300
C14—C151.367 (5)C29—C301.362 (5)
C15—H150.9300C30—H300.9300
C4—O2—H2109.6C19—O5—H5109.6
C6—O3—C9117.5 (3)C21—O6—C24118.8 (3)
C2—C1—H1A109.5C17—C16—H16A109.5
C2—C1—H1B109.5C17—C16—H16B109.5
H1A—C1—H1B109.5H16A—C16—H16B109.5
C2—C1—H1C109.5C17—C16—H16C109.5
H1A—C1—H1C109.5H16A—C16—H16C109.5
H1B—C1—H1C109.5H16B—C16—H16C109.5
O1—C2—C3120.9 (4)O4—C17—C18120.3 (4)
O1—C2—C1119.1 (3)O4—C17—C16118.8 (3)
C3—C2—C1120.0 (4)C18—C17—C16120.9 (4)
C8—C3—C4116.5 (3)C23—C18—C19116.9 (3)
C8—C3—C2123.5 (3)C23—C18—C17122.7 (4)
C4—C3—C2119.9 (3)C19—C18—C17120.3 (4)
O2—C4—C5117.6 (3)O5—C19—C20117.6 (4)
O2—C4—C3121.1 (3)O5—C19—C18120.9 (3)
C5—C4—C3121.3 (3)C20—C19—C18121.5 (4)
C6—C5—C4120.2 (3)C19—C20—C21119.5 (4)
C6—C5—H5A119.9C19—C20—H20120.2
C4—C5—H5A119.9C21—C20—H20120.2
O3—C6—C5124.9 (3)O6—C21—C20124.0 (3)
O3—C6—C7115.0 (3)O6—C21—C22115.8 (3)
C5—C6—C7120.1 (3)C20—C21—C22120.2 (3)
C8—C7—C6119.6 (3)C23—C22—C21120.0 (4)
C8—C7—H7120.2C23—C22—H22120.0
C6—C7—H7120.2C21—C22—H22120.0
C7—C8—C3122.4 (3)C22—C23—C18121.8 (4)
C7—C8—H8118.8C22—C23—H23119.1
C3—C8—H8118.8C18—C23—H23119.1
O3—C9—C10109.5 (3)O6—C24—C25109.5 (3)
O3—C9—H9A109.8O6—C24—H24A109.8
C10—C9—H9A109.8C25—C24—H24A109.8
O3—C9—H9B109.8O6—C24—H24B109.8
C10—C9—H9B109.8C25—C24—H24B109.8
H9A—C9—H9B108.2H24A—C24—H24B108.2
C15—C10—C11119.1 (3)C30—C25—C26118.7 (3)
C15—C10—C9122.8 (3)C30—C25—C24118.8 (4)
C11—C10—C9118.1 (3)C26—C25—C24122.5 (3)
C12—C11—C10119.2 (4)C27—C26—C25119.3 (4)
C12—C11—H11120.4C27—C26—H26120.4
C10—C11—H11120.4C25—C26—H26120.4
F1—C12—C11119.1 (4)F3—C27—C26118.6 (4)
F1—C12—C13117.5 (4)F3—C27—C28117.7 (3)
C11—C12—C13123.4 (4)C26—C27—C28123.7 (4)
C12—C13—C14115.6 (3)C29—C28—C27115.1 (3)
C12—C13—H13122.2C29—C28—H28122.4
C14—C13—H13122.2C27—C28—H28122.4
F2—C14—C15118.8 (4)F4—C29—C30118.7 (4)
F2—C14—C13117.7 (3)F4—C29—C28117.4 (3)
C15—C14—C13123.5 (4)C30—C29—C28124.0 (4)
C14—C15—C10119.1 (4)C29—C30—C25119.2 (4)
C14—C15—H15120.5C29—C30—H30120.4
C10—C15—H15120.5C25—C30—H30120.4
O1—C2—C3—C8179.7 (4)O4—C17—C18—C23178.5 (4)
C1—C2—C3—C81.2 (6)C16—C17—C18—C23−0.8 (6)
O1—C2—C3—C4−2.9 (6)O4—C17—C18—C19−2.0 (6)
C1—C2—C3—C4178.6 (4)C16—C17—C18—C19178.6 (4)
C8—C3—C4—O2180.0 (3)C23—C18—C19—O5−179.4 (3)
C2—C3—C4—O22.4 (5)C17—C18—C19—O51.2 (6)
C8—C3—C4—C5−0.7 (5)C23—C18—C19—C201.5 (5)
C2—C3—C4—C5−178.2 (3)C17—C18—C19—C20−178.0 (3)
O2—C4—C5—C6−179.9 (3)O5—C19—C20—C21−179.9 (3)
C3—C4—C5—C60.7 (6)C18—C19—C20—C21−0.7 (6)
C9—O3—C6—C50.7 (5)C24—O6—C21—C200.5 (5)
C9—O3—C6—C7−179.6 (3)C24—O6—C21—C22179.9 (3)
C4—C5—C6—O3178.9 (3)C19—C20—C21—O6178.9 (3)
C4—C5—C6—C7−0.8 (5)C19—C20—C21—C22−0.6 (6)
O3—C6—C7—C8−178.9 (3)O6—C21—C22—C23−178.5 (3)
C5—C6—C7—C80.8 (6)C20—C21—C22—C231.0 (6)
C6—C7—C8—C3−0.8 (6)C21—C22—C23—C18−0.1 (6)
C4—C3—C8—C70.7 (5)C19—C18—C23—C22−1.1 (5)
C2—C3—C8—C7178.2 (4)C17—C18—C23—C22178.4 (4)
C6—O3—C9—C10178.5 (3)C21—O6—C24—C25178.4 (3)
O3—C9—C10—C152.3 (5)O6—C24—C25—C30−179.6 (3)
O3—C9—C10—C11−178.3 (3)O6—C24—C25—C260.1 (5)
C15—C10—C11—C12−0.5 (6)C30—C25—C26—C27−0.9 (6)
C9—C10—C11—C12−180.0 (4)C24—C25—C26—C27179.5 (4)
C10—C11—C12—F1179.8 (4)C25—C26—C27—F3−179.6 (4)
C10—C11—C12—C131.2 (7)C25—C26—C27—C280.5 (7)
F1—C12—C13—C14179.8 (4)F3—C27—C28—C29−180.0 (4)
C11—C12—C13—C14−1.6 (6)C26—C27—C28—C29−0.1 (7)
C12—C13—C14—F2179.9 (4)C27—C28—C29—F4179.9 (4)
C12—C13—C14—C151.5 (6)C27—C28—C29—C300.0 (6)
F2—C14—C15—C10−179.4 (4)F4—C29—C30—C25179.7 (4)
C13—C14—C15—C10−1.0 (6)C28—C29—C30—C25−0.3 (7)
C11—C10—C15—C140.5 (6)C26—C25—C30—C290.8 (6)
C9—C10—C15—C14179.9 (4)C24—C25—C30—C29−179.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.812.533 (4)147.
O5—H5···O40.821.802.525 (4)147.
C8—H8···O50.932.493.382 (5)161.
C13—H13···O1i0.932.443.342 (5)165.
C28—H28···O4ii0.932.403.315 (5)168.

Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2156).

References

  • Dermer, O. C. (1934). Chem. Rev.14, 385–430.
  • Ma, Y.-T., Wang, J.-J., Liu, X.-W., Yang, S.-X. & Gao, J.-M. (2010). Acta Cryst. E66, o52. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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