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Crystals of the title compound, C14H10FNO2, show paired N—H...O hydrogen bonds that link the mol­ecules into R22(12) dimers; the hydrogen-bonded dimers are linked into chains by an aromatic π–π stacking inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031783/om2039sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031783/om2039Isup2.hkl
Contains datablock I

CCDC reference: 621455

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.050
  • wR factor = 0.133
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(4-fluoroanilino)isobenzofuran-1(3H)-one top
Crystal data top
C14H10FNO2Z = 2
Mr = 243.23F(000) = 252
Triclinic, P1Dx = 1.443 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0041 (8) ÅCell parameters from 5837 reflections
b = 8.1023 (9) Åθ = 3.2–27.9°
c = 10.2114 (12) ŵ = 0.11 mm1
α = 91.433 (9)°T = 296 K
β = 93.906 (9)°Prism, colorless
γ = 104.300 (9)°0.48 × 0.24 × 0.11 mm
V = 559.71 (11) Å3
Data collection top
Stoe IPDS-2
diffractometer
2202 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1475 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.086
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.2°
ω scansh = 88
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 99
Tmin = 0.963, Tmax = 0.988l = 1212
7292 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0718P)2]
where P = (Fo2 + 2Fc2)/3
2202 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.18 e Å3
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
C10.2513 (3)0.4589 (2)0.55093 (19)0.0478 (4)
C20.2533 (3)0.2814 (2)0.52252 (19)0.0472 (4)
C30.2825 (3)0.1574 (3)0.6068 (2)0.0580 (5)
H30.30790.18090.69680.070*
C40.2727 (3)0.0019 (3)0.5528 (2)0.0638 (6)
H40.28870.08870.60710.077*
C50.2392 (3)0.0342 (3)0.4189 (2)0.0629 (6)
H50.23510.14260.38450.075*
C60.2116 (3)0.0898 (2)0.3344 (2)0.0557 (5)
H60.19030.06720.24410.067*
C70.2170 (3)0.2479 (2)0.38889 (19)0.0463 (4)
C80.1799 (3)0.4028 (2)0.32502 (18)0.0477 (5)
H80.04180.37790.28940.057*
C90.2712 (3)0.5906 (2)0.14299 (17)0.0456 (4)
C100.4181 (3)0.6646 (2)0.0633 (2)0.0558 (5)
H100.53860.63540.07120.067*
C110.3894 (4)0.7811 (3)0.0277 (2)0.0666 (6)
H110.48760.82840.08240.080*
C120.2140 (4)0.8249 (3)0.0353 (2)0.0632 (6)
C130.0670 (3)0.7590 (3)0.0429 (2)0.0612 (6)
H130.05100.79240.03590.073*
C140.0959 (3)0.6411 (3)0.13331 (19)0.0542 (5)
H140.00310.59560.18790.065*
N10.3027 (3)0.4624 (2)0.22547 (16)0.0513 (4)
O10.2815 (2)0.53909 (19)0.65512 (14)0.0610 (4)
O20.2102 (2)0.52957 (16)0.43813 (13)0.0522 (4)
F10.1839 (3)0.9402 (2)0.12504 (15)0.0965 (5)
H10.422 (3)0.459 (3)0.2447 (19)0.050 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0415 (10)0.0514 (10)0.0509 (11)0.0118 (8)0.0049 (8)0.0040 (9)
C20.0390 (10)0.0483 (10)0.0546 (11)0.0102 (8)0.0047 (8)0.0102 (8)
C30.0501 (12)0.0630 (13)0.0619 (13)0.0142 (10)0.0045 (9)0.0207 (10)
C40.0535 (13)0.0542 (13)0.0864 (17)0.0162 (10)0.0054 (11)0.0276 (11)
C50.0554 (13)0.0432 (11)0.0916 (17)0.0153 (9)0.0038 (11)0.0076 (10)
C60.0517 (12)0.0475 (11)0.0663 (13)0.0107 (9)0.0004 (9)0.0002 (9)
C70.0399 (10)0.0449 (10)0.0539 (11)0.0101 (8)0.0020 (8)0.0079 (8)
C80.0472 (11)0.0472 (10)0.0487 (11)0.0126 (8)0.0011 (8)0.0041 (8)
C90.0543 (11)0.0426 (9)0.0405 (9)0.0144 (8)0.0017 (8)0.0004 (7)
C100.0617 (13)0.0504 (11)0.0577 (12)0.0171 (10)0.0081 (9)0.0054 (9)
C110.0823 (17)0.0584 (12)0.0601 (13)0.0155 (12)0.0169 (11)0.0132 (10)
C120.0886 (17)0.0513 (11)0.0511 (12)0.0214 (11)0.0030 (11)0.0122 (9)
C130.0670 (14)0.0602 (12)0.0607 (13)0.0262 (11)0.0058 (10)0.0071 (10)
C140.0561 (12)0.0578 (11)0.0521 (11)0.0200 (10)0.0051 (9)0.0078 (9)
N10.0492 (10)0.0574 (10)0.0512 (9)0.0203 (8)0.0032 (7)0.0106 (7)
O10.0570 (9)0.0697 (9)0.0567 (9)0.0180 (7)0.0022 (7)0.0044 (7)
O20.0614 (9)0.0458 (7)0.0528 (8)0.0190 (6)0.0049 (6)0.0071 (6)
F10.1258 (14)0.0879 (10)0.0835 (10)0.0382 (9)0.0045 (9)0.0439 (8)
Geometric parameters (Å, º) top
C1—O11.211 (2)C8—O21.495 (2)
C1—O21.344 (2)C8—H80.9800
C1—C21.464 (3)C9—C101.383 (3)
C2—C71.378 (3)C9—C141.385 (3)
C2—C31.383 (3)C9—N11.404 (2)
C3—C41.375 (3)C10—C111.381 (3)
C3—H30.9300C10—H100.9300
C4—C51.379 (3)C11—C121.358 (3)
C4—H40.9300C11—H110.9300
C5—C61.381 (3)C12—C131.358 (3)
C5—H50.9300C12—F11.368 (2)
C6—C71.375 (3)C13—C141.385 (3)
C6—H60.9300C13—H130.9300
C7—C81.499 (2)C14—H140.9300
C8—N11.395 (2)N1—H10.85 (2)
O1—C1—O2121.79 (18)O2—C8—H8109.1
O1—C1—C2129.23 (18)C7—C8—H8109.1
O2—C1—C2108.97 (16)C10—C9—C14118.39 (18)
C7—C2—C3121.58 (19)C10—C9—N1118.62 (17)
C7—C2—C1108.42 (16)C14—C9—N1122.92 (18)
C3—C2—C1130.00 (19)C11—C10—C9121.3 (2)
C4—C3—C2117.6 (2)C11—C10—H10119.4
C4—C3—H3121.2C9—C10—H10119.4
C2—C3—H3121.2C12—C11—C10118.3 (2)
C3—C4—C5120.68 (19)C12—C11—H11120.9
C3—C4—H4119.7C10—C11—H11120.9
C5—C4—H4119.7C11—C12—C13122.66 (19)
C4—C5—C6121.8 (2)C11—C12—F1118.8 (2)
C4—C5—H5119.1C13—C12—F1118.6 (2)
C6—C5—H5119.1C12—C13—C14118.8 (2)
C7—C6—C5117.4 (2)C12—C13—H13120.6
C7—C6—H6121.3C14—C13—H13120.6
C5—C6—H6121.3C9—C14—C13120.5 (2)
C6—C7—C2120.86 (18)C9—C14—H14119.7
C6—C7—C8129.85 (18)C13—C14—H14119.7
C2—C7—C8109.24 (16)C8—N1—C9122.22 (16)
N1—C8—O2111.97 (15)C8—N1—H1112.5 (14)
N1—C8—C7114.57 (16)C9—N1—H1117.3 (14)
O2—C8—C7102.66 (14)C1—O2—C8110.63 (14)
N1—C8—H8109.1
O1—C1—C2—C7177.98 (19)C14—C9—C10—C112.6 (3)
O2—C1—C2—C71.5 (2)N1—C9—C10—C11174.53 (18)
O1—C1—C2—C32.7 (3)C9—C10—C11—C121.5 (3)
O2—C1—C2—C3177.8 (2)C10—C11—C12—C130.1 (3)
C7—C2—C3—C40.5 (3)C10—C11—C12—F1180.0 (2)
C1—C2—C3—C4178.75 (18)C11—C12—C13—C140.6 (3)
C2—C3—C4—C51.4 (3)F1—C12—C13—C14179.51 (19)
C3—C4—C5—C60.9 (3)C10—C9—C14—C132.0 (3)
C4—C5—C6—C70.6 (3)N1—C9—C14—C13174.97 (18)
C5—C6—C7—C21.5 (3)C12—C13—C14—C90.4 (3)
C5—C6—C7—C8175.63 (19)O2—C8—N1—C972.7 (2)
C3—C2—C7—C61.0 (3)C7—C8—N1—C9170.92 (16)
C1—C2—C7—C6179.60 (17)C10—C9—N1—C8168.26 (18)
C3—C2—C7—C8176.66 (18)C14—C9—N1—C814.8 (3)
C1—C2—C7—C82.7 (2)O1—C1—O2—C8179.91 (17)
C6—C7—C8—N158.1 (3)C2—C1—O2—C80.41 (19)
C2—C7—C8—N1124.45 (18)N1—C8—O2—C1125.31 (16)
C6—C7—C8—O2179.77 (18)C7—C8—O2—C11.94 (18)
C2—C7—C8—O22.83 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (2)2.25 (2)3.082 (2)166.2 (18)
Symmetry code: (i) x+1, y+1, z+1.
 

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