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In the title mol­ecule, C15H9F3O2, the bond lengths and angles are within normal ranges. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009967/cv6485sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009967/cv6485Isup2.hkl
Contains datablock I

CCDC reference: 271854

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.130
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 - C5 .. 6.52 su PLAT230_ALERT_2_C Hirshfeld Test Diff for F3 - C11 .. 5.08 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(2,4-Difluorophenyl)-1-[3-(2-fluorophenyl)oxiran-2-yl]methanone top
Crystal data top
C15H9F3O2F(000) = 568
Mr = 278.22Dx = 1.502 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1564 reflections
a = 12.429 (2) Åθ = 2.3–22.0°
b = 13.359 (2) ŵ = 0.13 mm1
c = 7.6176 (13) ÅT = 293 K
β = 103.414 (2)°Block, colourless
V = 1230.3 (3) Å30.24 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2949 independent reflections
Radiation source: fine-focus sealed tube1765 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.962, Tmax = 0.980k = 1017
8121 measured reflectionsl = 109
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0455P)2 + 0.1661P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2949 reflectionsΔρmax = 0.35 e Å3
182 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (2)
Special details top

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) top
xyzUiso*/Ueq
F10.81756 (10)0.89450 (10)1.11670 (16)0.0809 (4)
F21.18486 (13)0.88377 (14)1.4288 (2)0.1204 (6)
F30.57299 (10)1.08497 (8)0.71041 (17)0.0764 (4)
O10.68732 (11)0.80742 (11)0.59757 (17)0.0707 (4)
O20.90216 (12)0.86316 (12)0.63525 (17)0.0768 (5)
C10.66766 (15)0.89997 (14)0.6774 (2)0.0534 (4)
H10.69400.95980.62590.064*
C20.75438 (14)0.83042 (13)0.7703 (2)0.0526 (4)
H20.73980.79320.87320.063*
C30.87209 (15)0.85466 (13)0.7750 (2)0.0526 (4)
C40.95245 (14)0.86570 (12)0.9517 (2)0.0487 (4)
C50.92424 (15)0.88237 (13)1.1140 (2)0.0540 (5)
C61.00030 (19)0.88967 (16)1.2762 (2)0.0701 (6)
H60.97900.90121.38370.084*
C71.10916 (19)0.87905 (17)1.2712 (3)0.0759 (6)
C81.14345 (17)0.86407 (17)1.1160 (3)0.0763 (6)
H81.21820.85831.11760.092*
C91.06495 (15)0.85775 (14)0.9582 (3)0.0614 (5)
H91.08740.84780.85120.074*
C100.56012 (14)0.91065 (14)0.7287 (2)0.0503 (4)
C110.51470 (14)1.00330 (14)0.7403 (2)0.0529 (4)
C120.41413 (16)1.01756 (16)0.7802 (2)0.0633 (5)
H120.38581.08160.78510.076*
C130.35630 (16)0.93542 (18)0.8127 (3)0.0697 (6)
H130.28750.94340.83930.084*
C140.39912 (18)0.84126 (18)0.8062 (3)0.0784 (6)
H140.35990.78570.83060.094*
C150.50009 (16)0.82868 (16)0.7636 (3)0.0671 (5)
H150.52820.76450.75820.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0741 (8)0.1035 (10)0.0752 (8)0.0033 (6)0.0379 (6)0.0184 (7)
F20.1110 (12)0.1458 (15)0.0815 (9)0.0391 (10)0.0242 (8)0.0303 (9)
F30.0868 (8)0.0542 (7)0.0941 (9)0.0009 (6)0.0329 (7)0.0083 (6)
O10.0734 (9)0.0762 (10)0.0600 (8)0.0066 (7)0.0103 (7)0.0248 (7)
O20.0852 (10)0.0990 (12)0.0551 (8)0.0042 (8)0.0342 (7)0.0037 (7)
C10.0650 (11)0.0519 (10)0.0429 (9)0.0037 (8)0.0118 (8)0.0023 (8)
C20.0614 (11)0.0523 (10)0.0453 (9)0.0018 (8)0.0148 (8)0.0011 (8)
C30.0637 (11)0.0485 (10)0.0505 (10)0.0076 (8)0.0233 (9)0.0012 (8)
C40.0568 (10)0.0407 (9)0.0533 (10)0.0026 (7)0.0224 (8)0.0040 (8)
C50.0599 (11)0.0504 (10)0.0575 (11)0.0034 (8)0.0254 (9)0.0002 (8)
C60.0987 (17)0.0676 (14)0.0462 (11)0.0202 (11)0.0213 (11)0.0029 (9)
C70.0749 (15)0.0746 (15)0.0683 (13)0.0191 (11)0.0033 (11)0.0199 (11)
C80.0569 (12)0.0775 (15)0.0924 (16)0.0004 (10)0.0132 (12)0.0186 (12)
C90.0609 (12)0.0595 (12)0.0677 (12)0.0030 (9)0.0233 (10)0.0061 (10)
C100.0552 (10)0.0518 (10)0.0411 (9)0.0020 (8)0.0052 (7)0.0022 (7)
C110.0597 (11)0.0516 (11)0.0447 (9)0.0021 (8)0.0066 (8)0.0032 (8)
C120.0628 (11)0.0667 (13)0.0584 (11)0.0127 (10)0.0104 (9)0.0006 (9)
C130.0515 (11)0.0848 (16)0.0715 (13)0.0015 (10)0.0116 (10)0.0033 (11)
C140.0669 (13)0.0704 (15)0.0969 (17)0.0155 (11)0.0172 (12)0.0019 (12)
C150.0675 (12)0.0513 (12)0.0820 (14)0.0010 (9)0.0162 (10)0.0040 (10)
Geometric parameters (Å, º) top
F1—C51.341 (2)C6—H60.9300
F2—C71.344 (2)C7—C81.361 (3)
F3—C111.358 (2)C8—C91.364 (3)
O1—C21.418 (2)C8—H80.9300
O1—C11.424 (2)C9—H90.9300
O2—C31.2124 (19)C10—C111.372 (2)
C1—C21.474 (2)C10—C151.385 (3)
C1—C101.484 (2)C11—C121.366 (3)
C1—H10.9800C12—C131.365 (3)
C2—C31.491 (3)C12—H120.9300
C2—H20.9800C13—C141.371 (3)
C3—C41.486 (2)C13—H130.9300
C4—C51.379 (2)C14—C151.377 (3)
C4—C91.392 (2)C14—H140.9300
C5—C61.374 (3)C15—H150.9300
C6—C71.370 (3)
C2—O1—C162.47 (11)F2—C7—C6117.5 (2)
O1—C1—C258.59 (11)C8—C7—C6123.4 (2)
O1—C1—C10116.76 (15)C7—C8—C9118.1 (2)
C2—C1—C10122.48 (15)C7—C8—H8121.0
O1—C1—H1115.6C9—C8—H8121.0
C2—C1—H1115.6C8—C9—C4122.26 (19)
C10—C1—H1115.6C8—C9—H9118.9
O1—C2—C158.94 (11)C4—C9—H9118.9
O1—C2—C3115.55 (14)C11—C10—C15116.93 (17)
C1—C2—C3118.60 (16)C11—C10—C1120.87 (16)
O1—C2—H2117.0C15—C10—C1122.19 (17)
C1—C2—H2117.0F3—C11—C12118.46 (17)
C3—C2—H2117.0F3—C11—C10118.07 (16)
O2—C3—C4120.45 (16)C12—C11—C10123.47 (17)
O2—C3—C2120.02 (16)C13—C12—C11118.38 (19)
C4—C3—C2119.51 (14)C13—C12—H12120.8
C5—C4—C9116.30 (17)C11—C12—H12120.8
C5—C4—C3124.82 (16)C12—C13—C14120.4 (2)
C9—C4—C3118.88 (15)C12—C13—H13119.8
F1—C5—C6117.02 (16)C14—C13—H13119.8
F1—C5—C4119.43 (17)C13—C14—C15120.2 (2)
C6—C5—C4123.54 (18)C13—C14—H14119.9
C7—C6—C5116.45 (19)C15—C14—H14119.9
C7—C6—H6121.8C14—C15—C10120.63 (19)
C5—C6—H6121.8C14—C15—H15119.7
F2—C7—C8119.2 (2)C10—C15—H15119.7
C2—O1—C1—C10113.38 (17)F2—C7—C8—C9178.83 (19)
C1—O1—C2—C3109.36 (18)C6—C7—C8—C91.1 (3)
C10—C1—C2—O1103.69 (18)C7—C8—C9—C40.2 (3)
O1—C1—C2—C3104.18 (17)C5—C4—C9—C81.2 (3)
C10—C1—C2—C3152.13 (16)C3—C4—C9—C8178.03 (18)
O1—C2—C3—O27.0 (3)O1—C1—C10—C11154.92 (15)
C1—C2—C3—O260.0 (2)C2—C1—C10—C11136.85 (18)
O1—C2—C3—C4171.46 (14)O1—C1—C10—C1523.8 (2)
C1—C2—C3—C4121.55 (17)C2—C1—C10—C1544.4 (2)
O2—C3—C4—C5162.97 (18)C15—C10—C11—F3178.67 (15)
C2—C3—C4—C518.6 (3)C1—C10—C11—F32.5 (2)
O2—C3—C4—C917.9 (3)C15—C10—C11—C121.4 (3)
C2—C3—C4—C9160.59 (16)C1—C10—C11—C12177.43 (15)
C9—C4—C5—F1177.55 (15)F3—C11—C12—C13179.14 (16)
C3—C4—C5—F13.3 (3)C10—C11—C12—C130.9 (3)
C9—C4—C5—C60.9 (3)C11—C12—C13—C140.4 (3)
C3—C4—C5—C6178.23 (17)C12—C13—C14—C151.2 (3)
F1—C5—C6—C7178.79 (17)C13—C14—C15—C100.7 (3)
C4—C5—C6—C70.3 (3)C11—C10—C15—C140.6 (3)
C5—C6—C7—F2178.60 (18)C1—C10—C15—C14178.25 (18)
C5—C6—C7—C81.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.982.383.356 (2)173
C6—H6···O2ii0.932.393.262 (2)157
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y, z+1.
 

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