3-(4-Fluoro­anilino)isobenzofuran-1(3H)-one

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.

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

No syntax errors found


No errors found in this datablock

---

Computing details

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

Crystal data

C14H10FNO2	Z = 2
Mr = 243.23	F(000) = 252
Triclinic, P1	Dx = 1.443 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0041 (8) Å	Cell parameters from 5837 reflections
b = 8.1023 (9) Å	θ = 3.2–27.9°
c = 10.2114 (12) Å	µ = 0.11 mm^−1
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) Å^3

Data collection

Stoe IPDS-2 diffractometer	2202 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1475 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.086
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.963, Tmax = 0.988	l = −12→12
7292 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0718P)^2] where P = (Fo^2 + 2Fc^2)/3
2202 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2513 (3)	0.4589 (2)	0.55093 (19)	0.0478 (4)
C2	0.2533 (3)	0.2814 (2)	0.52252 (19)	0.0472 (4)
C3	0.2825 (3)	0.1574 (3)	0.6068 (2)	0.0580 (5)
H3	0.3079	0.1809	0.6968	0.070*
C4	0.2727 (3)	−0.0019 (3)	0.5528 (2)	0.0638 (6)
H4	0.2887	−0.0887	0.6071	0.077*
C5	0.2392 (3)	−0.0342 (3)	0.4189 (2)	0.0629 (6)
H5	0.2351	−0.1426	0.3845	0.075*
C6	0.2116 (3)	0.0898 (2)	0.3344 (2)	0.0557 (5)
H6	0.1903	0.0672	0.2441	0.067*
C7	0.2170 (3)	0.2479 (2)	0.38889 (19)	0.0463 (4)
C8	0.1799 (3)	0.4028 (2)	0.32502 (18)	0.0477 (5)
H8	0.0418	0.3779	0.2894	0.057*
C9	0.2712 (3)	0.5906 (2)	0.14299 (17)	0.0456 (4)
C10	0.4181 (3)	0.6646 (2)	0.0633 (2)	0.0558 (5)
H10	0.5386	0.6354	0.0712	0.067*
C11	0.3894 (4)	0.7811 (3)	−0.0277 (2)	0.0666 (6)
H11	0.4876	0.8284	−0.0824	0.080*
C12	0.2140 (4)	0.8249 (3)	−0.0353 (2)	0.0632 (6)
C13	0.0670 (3)	0.7590 (3)	0.0429 (2)	0.0612 (6)
H13	−0.0510	0.7924	0.0359	0.073*
C14	0.0959 (3)	0.6411 (3)	0.13331 (19)	0.0542 (5)
H14	−0.0031	0.5956	0.1879	0.065*
N1	0.3027 (3)	0.4624 (2)	0.22547 (16)	0.0513 (4)
O1	0.2815 (2)	0.53909 (19)	0.65512 (14)	0.0610 (4)
O2	0.2102 (2)	0.52957 (16)	0.43813 (13)	0.0522 (4)
F1	0.1839 (3)	0.9402 (2)	−0.12504 (15)	0.0965 (5)
H1	0.422 (3)	0.459 (3)	0.2447 (19)	0.050 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0415 (10)	0.0514 (10)	0.0509 (11)	0.0118 (8)	0.0049 (8)	0.0040 (9)
C2	0.0390 (10)	0.0483 (10)	0.0546 (11)	0.0102 (8)	0.0047 (8)	0.0102 (8)
C3	0.0501 (12)	0.0630 (13)	0.0619 (13)	0.0142 (10)	0.0045 (9)	0.0207 (10)
C4	0.0535 (13)	0.0542 (13)	0.0864 (17)	0.0162 (10)	0.0054 (11)	0.0276 (11)
C5	0.0554 (13)	0.0432 (11)	0.0916 (17)	0.0153 (9)	0.0038 (11)	0.0076 (10)
C6	0.0517 (12)	0.0475 (11)	0.0663 (13)	0.0107 (9)	0.0004 (9)	−0.0002 (9)
C7	0.0399 (10)	0.0449 (10)	0.0539 (11)	0.0101 (8)	0.0020 (8)	0.0079 (8)
C8	0.0472 (11)	0.0472 (10)	0.0487 (11)	0.0126 (8)	0.0011 (8)	0.0041 (8)
C9	0.0543 (11)	0.0426 (9)	0.0405 (9)	0.0144 (8)	−0.0017 (8)	−0.0004 (7)
C10	0.0617 (13)	0.0504 (11)	0.0577 (12)	0.0171 (10)	0.0081 (9)	0.0054 (9)
C11	0.0823 (17)	0.0584 (12)	0.0601 (13)	0.0155 (12)	0.0169 (11)	0.0132 (10)
C12	0.0886 (17)	0.0513 (11)	0.0511 (12)	0.0214 (11)	−0.0030 (11)	0.0122 (9)
C13	0.0670 (14)	0.0602 (12)	0.0607 (13)	0.0262 (11)	−0.0058 (10)	0.0071 (10)
C14	0.0561 (12)	0.0578 (11)	0.0521 (11)	0.0200 (10)	0.0051 (9)	0.0078 (9)
N1	0.0492 (10)	0.0574 (10)	0.0512 (9)	0.0203 (8)	0.0032 (7)	0.0106 (7)
O1	0.0570 (9)	0.0697 (9)	0.0567 (9)	0.0180 (7)	0.0022 (7)	−0.0044 (7)
O2	0.0614 (9)	0.0458 (7)	0.0528 (8)	0.0190 (6)	0.0049 (6)	0.0071 (6)
F1	0.1258 (14)	0.0879 (10)	0.0835 (10)	0.0382 (9)	0.0045 (9)	0.0439 (8)

Geometric parameters (Å, º)

C1—O1	1.211 (2)	C8—O2	1.495 (2)
C1—O2	1.344 (2)	C8—H8	0.9800
C1—C2	1.464 (3)	C9—C10	1.383 (3)
C2—C7	1.378 (3)	C9—C14	1.385 (3)
C2—C3	1.383 (3)	C9—N1	1.404 (2)
C3—C4	1.375 (3)	C10—C11	1.381 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.379 (3)	C11—C12	1.358 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.381 (3)	C12—C13	1.358 (3)
C5—H5	0.9300	C12—F1	1.368 (2)
C6—C7	1.375 (3)	C13—C14	1.385 (3)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.499 (2)	C14—H14	0.9300
C8—N1	1.395 (2)	N1—H1	0.85 (2)
O1—C1—O2	121.79 (18)	O2—C8—H8	109.1
O1—C1—C2	129.23 (18)	C7—C8—H8	109.1
O2—C1—C2	108.97 (16)	C10—C9—C14	118.39 (18)
C7—C2—C3	121.58 (19)	C10—C9—N1	118.62 (17)
C7—C2—C1	108.42 (16)	C14—C9—N1	122.92 (18)
C3—C2—C1	130.00 (19)	C11—C10—C9	121.3 (2)
C4—C3—C2	117.6 (2)	C11—C10—H10	119.4
C4—C3—H3	121.2	C9—C10—H10	119.4
C2—C3—H3	121.2	C12—C11—C10	118.3 (2)
C3—C4—C5	120.68 (19)	C12—C11—H11	120.9
C3—C4—H4	119.7	C10—C11—H11	120.9
C5—C4—H4	119.7	C11—C12—C13	122.66 (19)
C4—C5—C6	121.8 (2)	C11—C12—F1	118.8 (2)
C4—C5—H5	119.1	C13—C12—F1	118.6 (2)
C6—C5—H5	119.1	C12—C13—C14	118.8 (2)
C7—C6—C5	117.4 (2)	C12—C13—H13	120.6
C7—C6—H6	121.3	C14—C13—H13	120.6
C5—C6—H6	121.3	C9—C14—C13	120.5 (2)
C6—C7—C2	120.86 (18)	C9—C14—H14	119.7
C6—C7—C8	129.85 (18)	C13—C14—H14	119.7
C2—C7—C8	109.24 (16)	C8—N1—C9	122.22 (16)
N1—C8—O2	111.97 (15)	C8—N1—H1	112.5 (14)
N1—C8—C7	114.57 (16)	C9—N1—H1	117.3 (14)
O2—C8—C7	102.66 (14)	C1—O2—C8	110.63 (14)
N1—C8—H8	109.1
O1—C1—C2—C7	−177.98 (19)	C14—C9—C10—C11	−2.6 (3)
O2—C1—C2—C7	1.5 (2)	N1—C9—C10—C11	174.53 (18)
O1—C1—C2—C3	2.7 (3)	C9—C10—C11—C12	1.5 (3)
O2—C1—C2—C3	−177.8 (2)	C10—C11—C12—C13	0.1 (3)
C7—C2—C3—C4	−0.5 (3)	C10—C11—C12—F1	180.0 (2)
C1—C2—C3—C4	178.75 (18)	C11—C12—C13—C14	−0.6 (3)
C2—C3—C4—C5	1.4 (3)	F1—C12—C13—C14	179.51 (19)
C3—C4—C5—C6	−0.9 (3)	C10—C9—C14—C13	2.0 (3)
C4—C5—C6—C7	−0.6 (3)	N1—C9—C14—C13	−174.97 (18)
C5—C6—C7—C2	1.5 (3)	C12—C13—C14—C9	−0.4 (3)
C5—C6—C7—C8	−175.63 (19)	O2—C8—N1—C9	−72.7 (2)
C3—C2—C7—C6	−1.0 (3)	C7—C8—N1—C9	170.92 (16)
C1—C2—C7—C6	179.60 (17)	C10—C9—N1—C8	168.26 (18)
C3—C2—C7—C8	176.66 (18)	C14—C9—N1—C8	−14.8 (3)
C1—C2—C7—C8	−2.7 (2)	O1—C1—O2—C8	179.91 (17)
C6—C7—C8—N1	−58.1 (3)	C2—C1—O2—C8	0.41 (19)
C2—C7—C8—N1	124.45 (18)	N1—C8—O2—C1	−125.31 (16)
C6—C7—C8—O2	−179.77 (18)	C7—C8—O2—C1	−1.94 (18)
C2—C7—C8—O2	2.83 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.85 (2)	2.25 (2)	3.082 (2)	166.2 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.