Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049641/sj2371sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049641/sj2371Isup2.hkl |
CCDC reference: 667376
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.147
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.134 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O2 .. 3.24 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O1 .. 2.70 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O2 .. 2.70 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 5 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures, see: Büyükgüngör & Odabaşoğlu (2006a,b); Odabaşoğlu & Büyükgüngör (2007a,b,c, 2006a,b). For general background, see: Aoki et al. (1973); Lacova (1973); Elderfield (1951); Tsi & Tan (1997); Bellasio (1974); Roy & Sarkar (2005); Etter (1990).
The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006a), using phthalaldehydic acid and 2-hydroxy-5-chloroaniline as starting materials (yield 80%; m.p. 478–479 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol (95%) solution at room temperature.
All H atoms were located in a difference Fourier map and were refined freely with isotropic displacement parameters.
Phthalides (isobenzofuranones) possess several important properties, such as fungicidal (Aoki et al., 1973; Lacova, 1973), bactericidal and herbicidal (Lacova, 1973), analgesic (Elderfield, 1951), hypertensive and vasorelaxant activities (Tsi & Tan, 1997). In addition, phthalide derivatives are useful in the treatment of circulatory and heart-related diseases (Bellasio, 1974). They are also found to be associated with pesticidal activities (Roy & Sarkar, 2005). Considering the potential interest of such phthalide-3-phosphonates in synthetic organic chemistry, and as agrochemical and pharmaceutical agents, we decided to investigate the solid-state structures of 3-substituted phthalides by X-ray diffraction methods. As part of a continuing study of the interplay between molecular conformation and supramolecular aggregation in 3-substituted phthalides, we now report the structure of the title compound, 3-[2-(hydroxy-5-chloro)phenylamino]isobenzofuran-1(3H)-one, (I) (Fig. 1).
The geometry of the molecule of (I) does not show any significant differences from the average geometry found for 3-anilinoisobenzofuran-1(3H)-ones (Büyükgüngör & Odabaşoğlu, 2006a,b, 2007; Odabaşoğlu & Büyükgüngör, 2006a,b, 2007a,b). The phthalide group (C1–C8/O2) is planar, the largest deviation from the mean plane being -0.009 (1) Å for atom C7. The dihedral angle between the mean planes of the phthalide group and the phenyl ring is 76.8 (2)°.
In (I), the crystal packing is stabilized by C—H···O and N—H···O intermolecular hydrogen bonds (Fig. 2, Table 1), which generate R21(6)R44(27)R21(6) ring motifs (Etter, 1990). These motifs also generate a three dimensional network by C5—H5···Cg1 (Cg1 is the C9–C14 ring centroid), Table 1, and π···π interactions. - The π···π interaction occurs between the C2–C7 and C9–C14 rings and their symmetry-related counterparts at (x, 1/2 - y, 1/2 + z), with a centroid-to-centroid distance of 3.681 Å and a plane-to plane separation of 3.618 Å.
For related structures, see: Büyükgüngör & Odabaşoğlu (2006a,b); Odabaşoğlu & Büyükgüngör (2007a,b,c, 2006a,b). For general background, see: Aoki et al. (1973); Lacova (1973); Elderfield (1951); Tsi & Tan (1997); Bellasio (1974); Roy & Sarkar (2005); Etter (1990).
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).
C14H10ClNO3 | F(000) = 568 |
Mr = 275.68 | Dx = 1.502 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11707 reflections |
a = 9.0439 (6) Å | θ = 2.4–27.9° |
b = 11.5363 (10) Å | µ = 0.32 mm−1 |
c = 12.6602 (9) Å | T = 296 K |
β = 112.593 (5)° | Plate, colourless |
V = 1219.51 (16) Å3 | 0.53 × 0.39 × 0.13 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 2392 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1898 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.134 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −11→11 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.731, Tmax = 0.955 | l = −15→15 |
11707 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)] = 0.053 | All H-atom parameters refined |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0766P)2 + 0.1818P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2392 reflections | Δρmax = 0.32 e Å−3 |
213 parameters | Δρmin = −0.37 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: 0.008 (1) |
C14H10ClNO3 | V = 1219.51 (16) Å3 |
Mr = 275.68 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.0439 (6) Å | µ = 0.32 mm−1 |
b = 11.5363 (10) Å | T = 296 K |
c = 12.6602 (9) Å | 0.53 × 0.39 × 0.13 mm |
β = 112.593 (5)° |
Stoe IPDS 2 diffractometer | 2392 independent reflections |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | 1898 reflections with I > 2σ(I) |
Tmin = 0.731, Tmax = 0.955 | Rint = 0.134 |
11707 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.147 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.32 e Å−3 |
2392 reflections | Δρmin = −0.37 e Å−3 |
213 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 | 0.4753 (3) | 0.2984 (2) | 0.3612 (2) | 0.0528 (5) | |
C2 | 0.5622 (3) | 0.34482 (18) | 0.4771 (2) | 0.0492 (5) | |
C3 | 0.5358 (3) | 0.3266 (2) | 0.5766 (2) | 0.0584 (6) | |
C4 | 0.6373 (4) | 0.3805 (2) | 0.6741 (2) | 0.0619 (6) | |
C5 | 0.7624 (3) | 0.4495 (2) | 0.6728 (2) | 0.0620 (6) | |
C6 | 0.7886 (3) | 0.4667 (2) | 0.5734 (2) | 0.0598 (6) | |
C7 | 0.6855 (3) | 0.41331 (19) | 0.4756 (2) | 0.0491 (5) | |
C8 | 0.6824 (3) | 0.4165 (2) | 0.3563 (2) | 0.0520 (5) | |
C9 | 0.8505 (3) | 0.37712 (19) | 0.2471 (2) | 0.0495 (5) | |
C10 | 0.9761 (3) | 0.3099 (2) | 0.2418 (2) | 0.0534 (5) | |
C11 | 1.0103 (3) | 0.3104 (2) | 0.1448 (2) | 0.0578 (6) | |
C12 | 0.9220 (3) | 0.3779 (2) | 0.0514 (2) | 0.0575 (6) | |
C13 | 0.7988 (3) | 0.4440 (2) | 0.0573 (2) | 0.0545 (5) | |
C14 | 0.7618 (3) | 0.4443 (2) | 0.1535 (2) | 0.0535 (6) | |
N1 | 0.8247 (2) | 0.37584 (19) | 0.34941 (19) | 0.0557 (5) | |
O1 | 0.3639 (2) | 0.23271 (17) | 0.32605 (17) | 0.0680 (5) | |
O2 | 0.54328 (19) | 0.34162 (16) | 0.29172 (15) | 0.0578 (4) | |
O3 | 1.0593 (2) | 0.24668 (18) | 0.33773 (18) | 0.0673 (5) | |
Cl1 | 0.68573 (8) | 0.53075 (6) | −0.05833 (6) | 0.0703 (3) | |
H1 | 0.679 (3) | 0.489 (2) | 0.154 (2) | 0.051 (6)* | |
H2 | 1.091 (3) | 0.264 (2) | 0.141 (2) | 0.056 (7)* | |
H3 | 0.449 (3) | 0.279 (3) | 0.578 (2) | 0.072 (8)* | |
H4 | 0.654 (3) | 0.492 (2) | 0.320 (2) | 0.058 (7)* | |
H5 | 0.829 (3) | 0.485 (2) | 0.740 (2) | 0.063 (7)* | |
H6 | 0.873 (3) | 0.514 (2) | 0.575 (2) | 0.063 (7)* | |
H7 | 0.949 (3) | 0.383 (2) | −0.017 (3) | 0.071 (8)* | |
H8 | 0.626 (4) | 0.371 (3) | 0.743 (3) | 0.086 (10)* | |
H9 | 0.864 (3) | 0.320 (2) | 0.390 (2) | 0.052 (7)* | |
H10 | 1.147 (4) | 0.226 (3) | 0.339 (3) | 0.097 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0449 (11) | 0.0537 (12) | 0.0662 (14) | 0.0042 (10) | 0.0283 (10) | 0.0003 (10) |
C2 | 0.0474 (11) | 0.0472 (11) | 0.0587 (13) | 0.0058 (9) | 0.0268 (10) | 0.0013 (9) |
C3 | 0.0639 (14) | 0.0550 (13) | 0.0691 (15) | −0.0014 (11) | 0.0398 (13) | 0.0052 (11) |
C4 | 0.0826 (17) | 0.0532 (13) | 0.0594 (15) | 0.0075 (12) | 0.0377 (13) | 0.0042 (11) |
C5 | 0.0720 (15) | 0.0554 (13) | 0.0582 (14) | 0.0000 (12) | 0.0245 (12) | −0.0059 (11) |
C6 | 0.0613 (14) | 0.0575 (13) | 0.0662 (15) | −0.0063 (11) | 0.0307 (12) | −0.0043 (11) |
C7 | 0.0480 (11) | 0.0468 (11) | 0.0584 (13) | 0.0054 (9) | 0.0269 (10) | 0.0009 (9) |
C8 | 0.0495 (11) | 0.0543 (12) | 0.0596 (13) | 0.0001 (10) | 0.0291 (10) | −0.0017 (10) |
C9 | 0.0439 (11) | 0.0518 (11) | 0.0601 (13) | −0.0067 (9) | 0.0283 (10) | −0.0028 (10) |
C10 | 0.0464 (11) | 0.0512 (12) | 0.0687 (14) | −0.0044 (9) | 0.0288 (11) | 0.0000 (10) |
C11 | 0.0545 (13) | 0.0537 (12) | 0.0776 (16) | −0.0004 (10) | 0.0391 (12) | −0.0062 (11) |
C12 | 0.0589 (13) | 0.0596 (13) | 0.0647 (15) | −0.0096 (11) | 0.0358 (12) | −0.0084 (11) |
C13 | 0.0520 (12) | 0.0570 (12) | 0.0581 (13) | −0.0087 (10) | 0.0253 (10) | −0.0030 (10) |
C14 | 0.0450 (11) | 0.0577 (12) | 0.0644 (14) | −0.0008 (10) | 0.0286 (10) | −0.0016 (11) |
N1 | 0.0490 (10) | 0.0636 (12) | 0.0632 (12) | 0.0065 (9) | 0.0310 (9) | 0.0081 (10) |
O1 | 0.0509 (9) | 0.0766 (11) | 0.0786 (13) | −0.0112 (8) | 0.0274 (9) | −0.0126 (9) |
O2 | 0.0494 (8) | 0.0721 (10) | 0.0587 (10) | −0.0012 (7) | 0.0282 (7) | −0.0063 (8) |
O3 | 0.0554 (10) | 0.0744 (11) | 0.0813 (13) | 0.0143 (9) | 0.0366 (9) | 0.0147 (9) |
Cl1 | 0.0659 (4) | 0.0854 (5) | 0.0623 (4) | 0.0049 (3) | 0.0278 (3) | 0.0081 (3) |
C1—O1 | 1.201 (3) | C8—H4 | 0.98 (3) |
C1—O2 | 1.348 (3) | C9—C14 | 1.386 (3) |
C1—C2 | 1.474 (3) | C9—C10 | 1.398 (3) |
C2—C7 | 1.373 (3) | C9—N1 | 1.401 (3) |
C2—C3 | 1.385 (3) | C10—O3 | 1.368 (3) |
C3—C4 | 1.373 (4) | C10—C11 | 1.376 (4) |
C3—H3 | 0.96 (3) | C11—C12 | 1.385 (4) |
C4—C5 | 1.388 (4) | C11—H2 | 0.92 (3) |
C4—H8 | 0.93 (4) | C12—C13 | 1.374 (3) |
C5—C6 | 1.382 (4) | C12—H7 | 0.98 (3) |
C5—H5 | 0.93 (3) | C13—C14 | 1.381 (3) |
C6—C7 | 1.377 (3) | C13—Cl1 | 1.744 (3) |
C6—H6 | 0.94 (3) | C14—H1 | 0.92 (3) |
C7—C8 | 1.500 (3) | N1—H9 | 0.82 (3) |
C8—N1 | 1.404 (3) | O3—H10 | 0.83 (4) |
C8—O2 | 1.486 (3) | ||
O1—C1—O2 | 121.3 (2) | O2—C8—H4 | 104.3 (15) |
O1—C1—C2 | 130.5 (2) | C7—C8—H4 | 113.7 (16) |
O2—C1—C2 | 108.22 (19) | C14—C9—C10 | 118.9 (2) |
C7—C2—C3 | 121.7 (2) | C14—C9—N1 | 123.3 (2) |
C7—C2—C1 | 108.7 (2) | C10—C9—N1 | 117.8 (2) |
C3—C2—C1 | 129.6 (2) | O3—C10—C11 | 124.0 (2) |
C4—C3—C2 | 117.4 (2) | O3—C10—C9 | 115.6 (2) |
C4—C3—H3 | 120.6 (18) | C11—C10—C9 | 120.4 (2) |
C2—C3—H3 | 122.1 (18) | C10—C11—C12 | 120.7 (2) |
C3—C4—C5 | 121.0 (2) | C10—C11—H2 | 119.8 (16) |
C3—C4—H8 | 121 (2) | C12—C11—H2 | 119.5 (16) |
C5—C4—H8 | 118 (2) | C13—C12—C11 | 118.6 (2) |
C6—C5—C4 | 121.3 (3) | C13—C12—H7 | 119.5 (17) |
C6—C5—H5 | 119.6 (18) | C11—C12—H7 | 121.8 (17) |
C4—C5—H5 | 119.1 (18) | C12—C13—C14 | 121.7 (2) |
C7—C6—C5 | 117.5 (2) | C12—C13—Cl1 | 119.92 (19) |
C7—C6—H6 | 122.8 (18) | C14—C13—Cl1 | 118.39 (19) |
C5—C6—H6 | 119.7 (18) | C13—C14—C9 | 119.7 (2) |
C2—C7—C6 | 121.2 (2) | C13—C14—H1 | 119.2 (16) |
C2—C7—C8 | 109.1 (2) | C9—C14—H1 | 121.1 (16) |
C6—C7—C8 | 129.7 (2) | C9—N1—C8 | 122.4 (2) |
N1—C8—O2 | 111.98 (19) | C9—N1—H9 | 114.0 (19) |
N1—C8—C7 | 113.0 (2) | C8—N1—H9 | 114.4 (19) |
O2—C8—C7 | 102.92 (18) | C1—O2—C8 | 111.01 (18) |
N1—C8—H4 | 110.4 (16) | C10—O3—H10 | 111 (3) |
O1—C1—C2—C7 | 177.5 (2) | N1—C9—C10—O3 | 1.6 (3) |
O2—C1—C2—C7 | −1.8 (2) | C14—C9—C10—C11 | −0.3 (3) |
O1—C1—C2—C3 | −1.5 (4) | N1—C9—C10—C11 | −178.0 (2) |
O2—C1—C2—C3 | 179.2 (2) | O3—C10—C11—C12 | −179.1 (2) |
C7—C2—C3—C4 | 0.5 (3) | C9—C10—C11—C12 | 0.5 (4) |
C1—C2—C3—C4 | 179.4 (2) | C10—C11—C12—C13 | −0.4 (4) |
C2—C3—C4—C5 | −0.7 (4) | C11—C12—C13—C14 | 0.0 (4) |
C3—C4—C5—C6 | 0.3 (4) | C11—C12—C13—Cl1 | 179.65 (18) |
C4—C5—C6—C7 | 0.3 (4) | C12—C13—C14—C9 | 0.2 (4) |
C3—C2—C7—C6 | 0.2 (3) | Cl1—C13—C14—C9 | −179.39 (17) |
C1—C2—C7—C6 | −179.0 (2) | C10—C9—C14—C13 | −0.1 (3) |
C3—C2—C7—C8 | −179.8 (2) | N1—C9—C14—C13 | 177.5 (2) |
C1—C2—C7—C8 | 1.1 (2) | C14—C9—N1—C8 | 17.8 (4) |
C5—C6—C7—C2 | −0.6 (4) | C10—C9—N1—C8 | −164.5 (2) |
C5—C6—C7—C8 | 179.3 (2) | O2—C8—N1—C9 | 67.8 (3) |
C2—C7—C8—N1 | −121.1 (2) | C7—C8—N1—C9 | −176.5 (2) |
C6—C7—C8—N1 | 59.0 (3) | O1—C1—O2—C8 | −177.6 (2) |
C2—C7—C8—O2 | −0.1 (2) | C2—C1—O2—C8 | 1.7 (2) |
C6—C7—C8—O2 | 180.0 (2) | N1—C8—O2—C1 | 120.7 (2) |
C14—C9—C10—O3 | 179.4 (2) | C7—C8—O2—C1 | −1.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H10···O1i | 0.83 (4) | 2.03 (4) | 2.820 (3) | 160 |
C11—H2···O1i | 0.92 (3) | 2.70 (3) | 3.265 (3) | 121 |
C4—H8···O2ii | 0.92 (4) | 2.70 (4) | 3.237 (3) | 117 |
C5—H5···Cg1iii | 0.93 (2) | 2.885 | 3.695 (3) | 146 |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2; (iii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H10ClNO3 |
Mr | 275.68 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 9.0439 (6), 11.5363 (10), 12.6602 (9) |
β (°) | 112.593 (5) |
V (Å3) | 1219.51 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.53 × 0.39 × 0.13 |
Data collection | |
Diffractometer | Stoe IPDS 2 |
Absorption correction | Integration (X-RED; Stoe & Cie, 2002) |
Tmin, Tmax | 0.731, 0.955 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11707, 2392, 1898 |
Rint | 0.134 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.147, 1.03 |
No. of reflections | 2392 |
No. of parameters | 213 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.32, −0.37 |
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 |
O3—H10···O1i | 0.83 (4) | 2.03 (4) | 2.820 (3) | 160 |
C11—H2···O1i | 0.92 (3) | 2.70 (3) | 3.265 (3) | 121 |
C4—H8···O2ii | 0.92 (4) | 2.70 (4) | 3.237 (3) | 117 |
C5—H5···Cg1iii | 0.93 (2) | 2.885 | 3.695 (3) | 146 |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2; (iii) −x+2, −y+1, −z+1. |
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Phthalides (isobenzofuranones) possess several important properties, such as fungicidal (Aoki et al., 1973; Lacova, 1973), bactericidal and herbicidal (Lacova, 1973), analgesic (Elderfield, 1951), hypertensive and vasorelaxant activities (Tsi & Tan, 1997). In addition, phthalide derivatives are useful in the treatment of circulatory and heart-related diseases (Bellasio, 1974). They are also found to be associated with pesticidal activities (Roy & Sarkar, 2005). Considering the potential interest of such phthalide-3-phosphonates in synthetic organic chemistry, and as agrochemical and pharmaceutical agents, we decided to investigate the solid-state structures of 3-substituted phthalides by X-ray diffraction methods. As part of a continuing study of the interplay between molecular conformation and supramolecular aggregation in 3-substituted phthalides, we now report the structure of the title compound, 3-[2-(hydroxy-5-chloro)phenylamino]isobenzofuran-1(3H)-one, (I) (Fig. 1).
The geometry of the molecule of (I) does not show any significant differences from the average geometry found for 3-anilinoisobenzofuran-1(3H)-ones (Büyükgüngör & Odabaşoğlu, 2006a,b, 2007; Odabaşoğlu & Büyükgüngör, 2006a,b, 2007a,b). The phthalide group (C1–C8/O2) is planar, the largest deviation from the mean plane being -0.009 (1) Å for atom C7. The dihedral angle between the mean planes of the phthalide group and the phenyl ring is 76.8 (2)°.
In (I), the crystal packing is stabilized by C—H···O and N—H···O intermolecular hydrogen bonds (Fig. 2, Table 1), which generate R21(6)R44(27)R21(6) ring motifs (Etter, 1990). These motifs also generate a three dimensional network by C5—H5···Cg1 (Cg1 is the C9–C14 ring centroid), Table 1, and π···π interactions. - The π···π interaction occurs between the C2–C7 and C9–C14 rings and their symmetry-related counterparts at (x, 1/2 - y, 1/2 + z), with a centroid-to-centroid distance of 3.681 Å and a plane-to plane separation of 3.618 Å.