Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051483/at2436sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051483/at2436Isup2.hkl |
CCDC reference: 667419
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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).
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.
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.
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).
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).
C14H10FNO2 | Z = 2 |
Mr = 243.23 | F(000) = 252 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0942 (18) Å | Cell parameters from 19681 reflections |
b = 7.984 (2) Å | θ = 2.0–28.1° |
c = 10.092 (4) Å | µ = 0.11 mm−1 |
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 |
Stoe IPDS-2 diffractometer | 2167 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1822 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.037 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
ω scans | h = −8→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −9→9 |
Tmin = 0.945, Tmax = 0.968 | l = −12→12 |
9227 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H 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 reflections | Δρmax = 0.15 e Å−3 |
168 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.157 (9) |
C14H10FNO2 | γ = 74.93 (2)° |
Mr = 243.23 | V = 549.7 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0942 (18) Å | Mo Kα radiation |
b = 7.984 (2) Å | µ = 0.11 mm−1 |
c = 10.092 (4) Å | T = 296 K |
α = 88.92 (3)° | 0.62 × 0.52 × 0.38 mm |
β = 84.84 (3)° |
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 = 0.968 | Rint = 0.037 |
9227 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.15 e Å−3 |
2167 reflections | Δρmin = −0.12 e Å−3 |
168 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.74814 (17) | 0.46754 (16) | 0.55003 (12) | 0.0453 (3) | |
C2 | 0.74694 (16) | 0.28901 (15) | 0.51978 (12) | 0.0439 (3) | |
C3 | 0.71836 (19) | 0.15804 (18) | 0.60483 (14) | 0.0538 (3) | |
H3 | 0.6942 | 0.1762 | 0.6962 | 0.065* | |
C4 | 0.7270 (2) | 0.00029 (18) | 0.54906 (16) | 0.0596 (4) | |
H4 | 0.7108 | −0.0911 | 0.6035 | 0.072* | |
C5 | 0.75954 (19) | −0.02397 (17) | 0.41274 (16) | 0.0587 (4) | |
H5 | 0.7631 | −0.1315 | 0.3773 | 0.070* | |
C6 | 0.78691 (18) | 0.10685 (16) | 0.32784 (14) | 0.0515 (3) | |
H6 | 0.8079 | 0.0897 | 0.2362 | 0.062* | |
C7 | 0.78179 (16) | 0.26420 (15) | 0.38439 (12) | 0.0431 (3) | |
C8 | 0.81902 (17) | 0.42464 (15) | 0.32039 (12) | 0.0435 (3) | |
H8 | 0.9558 | 0.3995 | 0.2829 | 0.052* | |
C9 | 0.73725 (17) | 0.61732 (15) | 0.13090 (11) | 0.0420 (3) | |
C10 | 0.59784 (17) | 0.69605 (16) | 0.04574 (13) | 0.0477 (3) | |
C11 | 0.6292 (2) | 0.80564 (19) | −0.05390 (14) | 0.0581 (4) | |
H11 | 0.5326 | 0.8517 | −0.1107 | 0.070* | |
C12 | 0.8064 (2) | 0.84704 (18) | −0.06903 (14) | 0.0602 (4) | |
H12 | 0.8311 | 0.9218 | −0.1363 | 0.072* | |
C13 | 0.9464 (2) | 0.77698 (18) | 0.01608 (13) | 0.0546 (3) | |
H13 | 1.0654 | 0.8064 | 0.0069 | 0.065* | |
C14 | 0.91375 (18) | 0.66372 (17) | 0.11494 (13) | 0.0485 (3) | |
H14 | 1.0107 | 0.6179 | 0.1715 | 0.058* | |
N1 | 0.69639 (16) | 0.49475 (14) | 0.22118 (10) | 0.0483 (3) | |
O1 | 0.71649 (14) | 0.54281 (13) | 0.65565 (9) | 0.0590 (3) | |
O2 | 0.79064 (13) | 0.54564 (11) | 0.43571 (8) | 0.0492 (2) | |
F1 | 0.42053 (11) | 0.65855 (12) | 0.06461 (9) | 0.0654 (3) | |
H15 | 0.577 (2) | 0.4864 (19) | 0.2323 (14) | 0.057 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0409 (6) | 0.0482 (7) | 0.0475 (7) | −0.0117 (5) | −0.0068 (5) | 0.0027 (5) |
C2 | 0.0378 (6) | 0.0431 (6) | 0.0504 (7) | −0.0092 (5) | −0.0063 (5) | 0.0053 (5) |
C3 | 0.0503 (7) | 0.0548 (8) | 0.0557 (7) | −0.0133 (6) | −0.0055 (6) | 0.0134 (6) |
C4 | 0.0532 (8) | 0.0473 (8) | 0.0793 (10) | −0.0159 (6) | −0.0056 (6) | 0.0186 (7) |
C5 | 0.0518 (7) | 0.0411 (7) | 0.0840 (10) | −0.0136 (6) | −0.0053 (7) | −0.0005 (6) |
C6 | 0.0479 (7) | 0.0468 (7) | 0.0595 (8) | −0.0120 (5) | −0.0029 (5) | −0.0037 (6) |
C7 | 0.0369 (6) | 0.0411 (6) | 0.0508 (7) | −0.0091 (5) | −0.0047 (5) | 0.0041 (5) |
C8 | 0.0430 (6) | 0.0425 (6) | 0.0456 (6) | −0.0119 (5) | −0.0039 (5) | 0.0015 (5) |
C9 | 0.0453 (6) | 0.0401 (6) | 0.0399 (6) | −0.0096 (5) | −0.0029 (5) | −0.0018 (5) |
C10 | 0.0427 (6) | 0.0488 (7) | 0.0506 (7) | −0.0094 (5) | −0.0062 (5) | −0.0018 (5) |
C11 | 0.0595 (8) | 0.0582 (8) | 0.0531 (8) | −0.0064 (6) | −0.0143 (6) | 0.0099 (6) |
C12 | 0.0686 (9) | 0.0559 (8) | 0.0537 (8) | −0.0138 (7) | −0.0023 (6) | 0.0140 (6) |
C13 | 0.0546 (7) | 0.0535 (7) | 0.0571 (8) | −0.0185 (6) | −0.0010 (6) | 0.0059 (6) |
C14 | 0.0477 (7) | 0.0501 (7) | 0.0491 (7) | −0.0141 (5) | −0.0088 (5) | 0.0050 (5) |
N1 | 0.0431 (6) | 0.0548 (6) | 0.0501 (6) | −0.0174 (5) | −0.0076 (4) | 0.0097 (5) |
O1 | 0.0645 (6) | 0.0625 (6) | 0.0518 (6) | −0.0194 (5) | −0.0044 (4) | −0.0071 (4) |
O2 | 0.0594 (5) | 0.0413 (5) | 0.0497 (5) | −0.0176 (4) | −0.0074 (4) | 0.0029 (4) |
F1 | 0.0466 (4) | 0.0767 (6) | 0.0755 (6) | −0.0177 (4) | −0.0155 (4) | 0.0098 (4) |
C1—O1 | 1.2077 (15) | C8—O2 | 1.4923 (15) |
C1—O2 | 1.3487 (16) | C8—H8 | 0.9800 |
C1—C2 | 1.4656 (18) | C9—C10 | 1.3861 (17) |
C2—C7 | 1.3752 (18) | C9—C14 | 1.3906 (17) |
C2—C3 | 1.3844 (18) | C9—N1 | 1.3922 (16) |
C3—C4 | 1.374 (2) | C10—C11 | 1.3617 (19) |
C3—H3 | 0.9300 | C10—F1 | 1.3633 (15) |
C4—C5 | 1.383 (2) | C11—C12 | 1.376 (2) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.3801 (19) | C12—C13 | 1.372 (2) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—C7 | 1.3801 (18) | C13—C14 | 1.3785 (18) |
C6—H6 | 0.9300 | C13—H13 | 0.9300 |
C7—C8 | 1.4972 (17) | C14—H14 | 0.9300 |
C8—N1 | 1.3982 (16) | N1—H15 | 0.862 (15) |
O1—C1—O2 | 121.89 (12) | O2—C8—H8 | 109.1 |
O1—C1—C2 | 129.46 (12) | C7—C8—H8 | 109.1 |
O2—C1—C2 | 108.65 (11) | C10—C9—C14 | 116.10 (11) |
C7—C2—C3 | 121.87 (12) | C10—C9—N1 | 119.13 (11) |
C7—C2—C1 | 108.46 (11) | C14—C9—N1 | 124.71 (11) |
C3—C2—C1 | 129.68 (12) | C11—C10—F1 | 119.38 (11) |
C4—C3—C2 | 117.46 (13) | C11—C10—C9 | 123.86 (12) |
C4—C3—H3 | 121.3 | F1—C10—C9 | 116.76 (11) |
C2—C3—H3 | 121.3 | C10—C11—C12 | 118.79 (12) |
C3—C4—C5 | 120.66 (13) | C10—C11—H11 | 120.6 |
C3—C4—H4 | 119.7 | C12—C11—H11 | 120.6 |
C5—C4—H4 | 119.7 | C13—C12—C11 | 119.35 (13) |
C6—C5—C4 | 121.90 (13) | C13—C12—H12 | 120.3 |
C6—C5—H5 | 119.1 | C11—C12—H12 | 120.3 |
C4—C5—H5 | 119.1 | C12—C13—C14 | 121.16 (13) |
C5—C6—C7 | 117.30 (13) | C12—C13—H13 | 119.4 |
C5—C6—H6 | 121.4 | C14—C13—H13 | 119.4 |
C7—C6—H6 | 121.4 | C13—C14—C9 | 120.65 (12) |
C2—C7—C6 | 120.81 (12) | C13—C14—H14 | 119.7 |
C2—C7—C8 | 109.45 (11) | C9—C14—H14 | 119.7 |
C6—C7—C8 | 129.68 (12) | C9—N1—C8 | 122.50 (11) |
N1—C8—O2 | 111.83 (10) | C9—N1—H15 | 117.7 (10) |
N1—C8—C7 | 114.81 (10) | C8—N1—H15 | 117.0 (10) |
O2—C8—C7 | 102.60 (9) | C1—O2—C8 | 110.74 (9) |
N1—C8—H8 | 109.1 | ||
O1—C1—C2—C7 | 176.95 (12) | C14—C9—C10—C11 | 3.59 (19) |
O2—C1—C2—C7 | −2.39 (13) | N1—C9—C10—C11 | −173.92 (12) |
O1—C1—C2—C3 | −3.4 (2) | C14—C9—C10—F1 | −176.78 (11) |
O2—C1—C2—C3 | 177.27 (12) | N1—C9—C10—F1 | 5.71 (17) |
C7—C2—C3—C4 | 0.32 (18) | F1—C10—C11—C12 | 177.82 (12) |
C1—C2—C3—C4 | −179.31 (12) | C9—C10—C11—C12 | −2.6 (2) |
C2—C3—C4—C5 | −1.2 (2) | C10—C11—C12—C13 | 0.1 (2) |
C3—C4—C5—C6 | 0.8 (2) | C11—C12—C13—C14 | 1.1 (2) |
C4—C5—C6—C7 | 0.4 (2) | C12—C13—C14—C9 | 0.0 (2) |
C3—C2—C7—C6 | 0.89 (18) | C10—C9—C14—C13 | −2.25 (18) |
C1—C2—C7—C6 | −179.41 (10) | N1—C9—C14—C13 | 175.10 (12) |
C3—C2—C7—C8 | −176.47 (11) | C10—C9—N1—C8 | −172.37 (11) |
C1—C2—C7—C8 | 3.23 (13) | C14—C9—N1—C8 | 10.35 (18) |
C5—C6—C7—C2 | −1.22 (18) | O2—C8—N1—C9 | 78.83 (14) |
C5—C6—C7—C8 | 175.54 (12) | C7—C8—N1—C9 | −164.80 (10) |
C2—C7—C8—N1 | −124.33 (12) | O1—C1—O2—C8 | −178.85 (11) |
C6—C7—C8—N1 | 58.62 (17) | C2—C1—O2—C8 | 0.55 (12) |
C2—C7—C8—O2 | −2.79 (12) | N1—C8—O2—C1 | 124.86 (11) |
C6—C7—C8—O2 | −179.84 (12) | C7—C8—O2—C1 | 1.30 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H15···O1i | 0.862 (15) | 2.344 (15) | 3.1627 (17) | 158.7 (13) |
C5—H5···O2ii | 0.93 | 2.59 | 3.3903 (18) | 144 |
C8—H8···O1iii | 0.98 | 2.61 | 3.4022 (17) | 138 |
C3—H3···F1i | 0.93 | 2.73 | 3.617 (2) | 161 |
C13—H13···F1iv | 0.93 | 2.60 | 3.3275 (18) | 135 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C14H10FNO2 |
Mr | 243.23 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 549.7 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.62 × 0.52 × 0.38 |
Data collection | |
Diffractometer | Stoe IPDS2 |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.945, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9227, 2167, 1822 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.085, 1.06 |
No. of reflections | 2167 |
No. of parameters | 168 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H15···O1i | 0.862 (15) | 2.344 (15) | 3.1627 (17) | 158.7 (13) |
C5—H5···O2ii | 0.93 | 2.59 | 3.3903 (18) | 143.9 |
C8—H8···O1iii | 0.98 | 2.61 | 3.4022 (17) | 137.6 |
C3—H3···F1i | 0.93 | 2.73 | 3.617 (2) | 160.6 |
C13—H13···F1iv | 0.93 | 2.60 | 3.3275 (18) | 135.2 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z. |
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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)°.