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The crystal structure of the title compound, C14H10FNO2, is stabilized by N—H...O, two C—H...O and two C—H...F inter­molecular hydrogen bonds. N—H...O, C—H...O and two C—H...F inter­molecular hydrogen bonds generate a fused R22(10)R22(12)R22(15)R32(13) ring motif. In the crystal structure, mol­ecules are linked into chains along the b axis by C—H...O hydrogen bonds. The dihedral angle between the phthalide group and the other benzene ring is 73.51 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051483/at2436sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051483/at2436Isup2.hkl
Contains datablock I

CCDC reference: 667419

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.085
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O1 .. 2.61 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. F1 .. 2.73 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. F1 .. 2.60 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of a continuing study of the interplay between molecular conformation and supramolecular aggregation in 3-substituted phthalides (Büyükgüngör & Odabaşoğlu, 2006a,b; Odabaşoğlu & Büyükgüngör, 2006a,b, 2007a,b), we now report the structure of 3-(4-butylphenylamino)isobenzofuran- 1(3H)-one, (I), (Fig. 1).

The crystal packing is stabilized by is stabilized by an N—H···O, two C—H···O and two C—H···F intermolecular hydrogen bonds (Table 1). In the structure, these hydrogen bond interactions generate an edge-fused R22(10)R22(12)R22(15)R32(13) ring motif (Fig. 2). The hydrogen bonded motifs are link each other C5—H5···O2 chains and forming three-dimentional network (Fig. 3). The phthalide group (C1—C8/O2) is planar, the largest deviation from the mean plane being -0.026 (4) Å for atom C6. The dihedral angle between the mean planes of the phthalide group and the phenyl ring is 73.51 (5)°.

Related literature top

For related structures, see: Büyükgüngör & Odabaşoğlu (2006a, 2006b); Odabaşoğlu & Büyükgüngör (2006a, 2006b, 2007a, 2007b). These compounds have fungicidal (Aoki et al., 1973; Lacova, 1973), bacterial and herbicidal (Lacova, 1973), analgesic (Elderfield, 1951), and hypotensive and vasorelaxant properties (Tsi & Tan, 1997).

Experimental top

Compound (I) was prepared as described by Odabaşoğlu & Büyükgüngör (2006a), using phthalaldehydic acid and 2-fluoroaniline as starting materials (yield 85%, m.p. 445–446 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a DMF-EtOH (1/1: v/v) solution at room temperature.

Refinement top

Except N-bound H, all C-bound H atoms were refined using the riding model approximation with d(C—H) = 0.93 for aromatic and d(C—H) = 0.98 for methine C—H [Uiso(H) = 1.2Ueq(parent atom)]. N-bound H atom was located in Fourier difference map and refined freely due to its taking part in H-bond.

Structure description top

As part of a continuing study of the interplay between molecular conformation and supramolecular aggregation in 3-substituted phthalides (Büyükgüngör & Odabaşoğlu, 2006a,b; Odabaşoğlu & Büyükgüngör, 2006a,b, 2007a,b), we now report the structure of 3-(4-butylphenylamino)isobenzofuran- 1(3H)-one, (I), (Fig. 1).

The crystal packing is stabilized by is stabilized by an N—H···O, two C—H···O and two C—H···F intermolecular hydrogen bonds (Table 1). In the structure, these hydrogen bond interactions generate an edge-fused R22(10)R22(12)R22(15)R32(13) ring motif (Fig. 2). The hydrogen bonded motifs are link each other C5—H5···O2 chains and forming three-dimentional network (Fig. 3). The phthalide group (C1—C8/O2) is planar, the largest deviation from the mean plane being -0.026 (4) Å for atom C6. The dihedral angle between the mean planes of the phthalide group and the phenyl ring is 73.51 (5)°.

For related structures, see: Büyükgüngör & Odabaşoğlu (2006a, 2006b); Odabaşoğlu & Büyükgüngör (2006a, 2006b, 2007a, 2007b). These compounds have fungicidal (Aoki et al., 1973; Lacova, 1973), bacterial and herbicidal (Lacova, 1973), analgesic (Elderfield, 1951), and hypotensive and vasorelaxant properties (Tsi & Tan, 1997).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).

Figures top
[Figure 1] Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level..
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of R22(10)R22(12)R22(15)R32(13) motifs. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) x - 1, y, z].
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of C6 chain along the c axis. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry code: (i) x, y + 1, z].
3-(2-Fluoroanilino)isobenzofuran-1(3H)-one top
Crystal data top
C14H10FNO2Z = 2
Mr = 243.23F(000) = 252
Triclinic, P1Dx = 1.469 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0942 (18) ÅCell parameters from 19681 reflections
b = 7.984 (2) Åθ = 2.0–28.1°
c = 10.092 (4) ŵ = 0.11 mm1
α = 88.92 (3)°T = 296 K
β = 84.84 (3)°Prism, colourless
γ = 74.93 (2)°0.62 × 0.52 × 0.38 mm
V = 549.7 (3) Å3
Data collection top
Stoe IPDS-2
diffractometer
2167 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1822 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.037
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 88
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 99
Tmin = 0.945, Tmax = 0.968l = 1212
9227 measured reflections
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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.0693P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2167 reflectionsΔρmax = 0.15 e Å3
168 parametersΔρmin = 0.12 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: 0.157 (9)
Crystal data top
C14H10FNO2γ = 74.93 (2)°
Mr = 243.23V = 549.7 (3) Å3
Triclinic, P1Z = 2
a = 7.0942 (18) ÅMo Kα radiation
b = 7.984 (2) ŵ = 0.11 mm1
c = 10.092 (4) ÅT = 296 K
α = 88.92 (3)°0.62 × 0.52 × 0.38 mm
β = 84.84 (3)°
Data collection top
Stoe IPDS-2
diffractometer
2167 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
1822 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.968Rint = 0.037
9227 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.15 e Å3
2167 reflectionsΔρmin = 0.12 e Å3
168 parameters
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
C10.74814 (17)0.46754 (16)0.55003 (12)0.0453 (3)
C20.74694 (16)0.28901 (15)0.51978 (12)0.0439 (3)
C30.71836 (19)0.15804 (18)0.60483 (14)0.0538 (3)
H30.69420.17620.69620.065*
C40.7270 (2)0.00029 (18)0.54906 (16)0.0596 (4)
H40.71080.09110.60350.072*
C50.75954 (19)0.02397 (17)0.41274 (16)0.0587 (4)
H50.76310.13150.37730.070*
C60.78691 (18)0.10685 (16)0.32784 (14)0.0515 (3)
H60.80790.08970.23620.062*
C70.78179 (16)0.26420 (15)0.38439 (12)0.0431 (3)
C80.81902 (17)0.42464 (15)0.32039 (12)0.0435 (3)
H80.95580.39950.28290.052*
C90.73725 (17)0.61732 (15)0.13090 (11)0.0420 (3)
C100.59784 (17)0.69605 (16)0.04574 (13)0.0477 (3)
C110.6292 (2)0.80564 (19)0.05390 (14)0.0581 (4)
H110.53260.85170.11070.070*
C120.8064 (2)0.84704 (18)0.06903 (14)0.0602 (4)
H120.83110.92180.13630.072*
C130.9464 (2)0.77698 (18)0.01608 (13)0.0546 (3)
H131.06540.80640.00690.065*
C140.91375 (18)0.66372 (17)0.11494 (13)0.0485 (3)
H141.01070.61790.17150.058*
N10.69639 (16)0.49475 (14)0.22118 (10)0.0483 (3)
O10.71649 (14)0.54281 (13)0.65565 (9)0.0590 (3)
O20.79064 (13)0.54564 (11)0.43571 (8)0.0492 (2)
F10.42053 (11)0.65855 (12)0.06461 (9)0.0654 (3)
H150.577 (2)0.4864 (19)0.2323 (14)0.057 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0409 (6)0.0482 (7)0.0475 (7)0.0117 (5)0.0068 (5)0.0027 (5)
C20.0378 (6)0.0431 (6)0.0504 (7)0.0092 (5)0.0063 (5)0.0053 (5)
C30.0503 (7)0.0548 (8)0.0557 (7)0.0133 (6)0.0055 (6)0.0134 (6)
C40.0532 (8)0.0473 (8)0.0793 (10)0.0159 (6)0.0056 (6)0.0186 (7)
C50.0518 (7)0.0411 (7)0.0840 (10)0.0136 (6)0.0053 (7)0.0005 (6)
C60.0479 (7)0.0468 (7)0.0595 (8)0.0120 (5)0.0029 (5)0.0037 (6)
C70.0369 (6)0.0411 (6)0.0508 (7)0.0091 (5)0.0047 (5)0.0041 (5)
C80.0430 (6)0.0425 (6)0.0456 (6)0.0119 (5)0.0039 (5)0.0015 (5)
C90.0453 (6)0.0401 (6)0.0399 (6)0.0096 (5)0.0029 (5)0.0018 (5)
C100.0427 (6)0.0488 (7)0.0506 (7)0.0094 (5)0.0062 (5)0.0018 (5)
C110.0595 (8)0.0582 (8)0.0531 (8)0.0064 (6)0.0143 (6)0.0099 (6)
C120.0686 (9)0.0559 (8)0.0537 (8)0.0138 (7)0.0023 (6)0.0140 (6)
C130.0546 (7)0.0535 (7)0.0571 (8)0.0185 (6)0.0010 (6)0.0059 (6)
C140.0477 (7)0.0501 (7)0.0491 (7)0.0141 (5)0.0088 (5)0.0050 (5)
N10.0431 (6)0.0548 (6)0.0501 (6)0.0174 (5)0.0076 (4)0.0097 (5)
O10.0645 (6)0.0625 (6)0.0518 (6)0.0194 (5)0.0044 (4)0.0071 (4)
O20.0594 (5)0.0413 (5)0.0497 (5)0.0176 (4)0.0074 (4)0.0029 (4)
F10.0466 (4)0.0767 (6)0.0755 (6)0.0177 (4)0.0155 (4)0.0098 (4)
Geometric parameters (Å, º) top
C1—O11.2077 (15)C8—O21.4923 (15)
C1—O21.3487 (16)C8—H80.9800
C1—C21.4656 (18)C9—C101.3861 (17)
C2—C71.3752 (18)C9—C141.3906 (17)
C2—C31.3844 (18)C9—N11.3922 (16)
C3—C41.374 (2)C10—C111.3617 (19)
C3—H30.9300C10—F11.3633 (15)
C4—C51.383 (2)C11—C121.376 (2)
C4—H40.9300C11—H110.9300
C5—C61.3801 (19)C12—C131.372 (2)
C5—H50.9300C12—H120.9300
C6—C71.3801 (18)C13—C141.3785 (18)
C6—H60.9300C13—H130.9300
C7—C81.4972 (17)C14—H140.9300
C8—N11.3982 (16)N1—H150.862 (15)
O1—C1—O2121.89 (12)O2—C8—H8109.1
O1—C1—C2129.46 (12)C7—C8—H8109.1
O2—C1—C2108.65 (11)C10—C9—C14116.10 (11)
C7—C2—C3121.87 (12)C10—C9—N1119.13 (11)
C7—C2—C1108.46 (11)C14—C9—N1124.71 (11)
C3—C2—C1129.68 (12)C11—C10—F1119.38 (11)
C4—C3—C2117.46 (13)C11—C10—C9123.86 (12)
C4—C3—H3121.3F1—C10—C9116.76 (11)
C2—C3—H3121.3C10—C11—C12118.79 (12)
C3—C4—C5120.66 (13)C10—C11—H11120.6
C3—C4—H4119.7C12—C11—H11120.6
C5—C4—H4119.7C13—C12—C11119.35 (13)
C6—C5—C4121.90 (13)C13—C12—H12120.3
C6—C5—H5119.1C11—C12—H12120.3
C4—C5—H5119.1C12—C13—C14121.16 (13)
C5—C6—C7117.30 (13)C12—C13—H13119.4
C5—C6—H6121.4C14—C13—H13119.4
C7—C6—H6121.4C13—C14—C9120.65 (12)
C2—C7—C6120.81 (12)C13—C14—H14119.7
C2—C7—C8109.45 (11)C9—C14—H14119.7
C6—C7—C8129.68 (12)C9—N1—C8122.50 (11)
N1—C8—O2111.83 (10)C9—N1—H15117.7 (10)
N1—C8—C7114.81 (10)C8—N1—H15117.0 (10)
O2—C8—C7102.60 (9)C1—O2—C8110.74 (9)
N1—C8—H8109.1
O1—C1—C2—C7176.95 (12)C14—C9—C10—C113.59 (19)
O2—C1—C2—C72.39 (13)N1—C9—C10—C11173.92 (12)
O1—C1—C2—C33.4 (2)C14—C9—C10—F1176.78 (11)
O2—C1—C2—C3177.27 (12)N1—C9—C10—F15.71 (17)
C7—C2—C3—C40.32 (18)F1—C10—C11—C12177.82 (12)
C1—C2—C3—C4179.31 (12)C9—C10—C11—C122.6 (2)
C2—C3—C4—C51.2 (2)C10—C11—C12—C130.1 (2)
C3—C4—C5—C60.8 (2)C11—C12—C13—C141.1 (2)
C4—C5—C6—C70.4 (2)C12—C13—C14—C90.0 (2)
C3—C2—C7—C60.89 (18)C10—C9—C14—C132.25 (18)
C1—C2—C7—C6179.41 (10)N1—C9—C14—C13175.10 (12)
C3—C2—C7—C8176.47 (11)C10—C9—N1—C8172.37 (11)
C1—C2—C7—C83.23 (13)C14—C9—N1—C810.35 (18)
C5—C6—C7—C21.22 (18)O2—C8—N1—C978.83 (14)
C5—C6—C7—C8175.54 (12)C7—C8—N1—C9164.80 (10)
C2—C7—C8—N1124.33 (12)O1—C1—O2—C8178.85 (11)
C6—C7—C8—N158.62 (17)C2—C1—O2—C80.55 (12)
C2—C7—C8—O22.79 (12)N1—C8—O2—C1124.86 (11)
C6—C7—C8—O2179.84 (12)C7—C8—O2—C11.30 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H15···O1i0.862 (15)2.344 (15)3.1627 (17)158.7 (13)
C5—H5···O2ii0.932.593.3903 (18)144
C8—H8···O1iii0.982.613.4022 (17)138
C3—H3···F1i0.932.733.617 (2)161
C13—H13···F1iv0.932.603.3275 (18)135
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x+2, y+1, z+1; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H10FNO2
Mr243.23
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.0942 (18), 7.984 (2), 10.092 (4)
α, β, γ (°)88.92 (3), 84.84 (3), 74.93 (2)
V3)549.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.62 × 0.52 × 0.38
Data collection
DiffractometerStoe IPDS2
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.945, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
9227, 2167, 1822
Rint0.037
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.085, 1.06
No. of reflections2167
No. of parameters168
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.12

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H15···O1i0.862 (15)2.344 (15)3.1627 (17)158.7 (13)
C5—H5···O2ii0.932.593.3903 (18)143.9
C8—H8···O1iii0.982.613.4022 (17)137.6
C3—H3···F1i0.932.733.617 (2)160.6
C13—H13···F1iv0.932.603.3275 (18)135.2
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x+2, y+1, z+1; (iv) x+1, y, z.
 

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