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The crystal structure of the title compound, C14H10ClNO3, is stabilized by inversion-related O—H...O and C—H...O inter­molecular hydrogen bonds and also by C—H...π and π–π inter­actions (centroid-to-centroid distance 3.681 Å and plane-to plane separation 3.618 Å). The O—H...O and C—H...O hydrogen bonds generate edge-fused R21(6)R44(27)R21(6) ring motifs. The phthalide part of the mol­ecule is planar and is inclined at 76.8 (2)° to the benzene ring of the amino­phenyl group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049641/sj2371sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049641/sj2371Isup2.hkl
Contains datablock I

CCDC reference: 667376

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

All H atoms were located in a difference Fourier map and were refined freely with isotropic displacement parameters.

Structure description top

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).

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 R21(6)R44(27)R21(6) motifs with hydrogen bonds shown as dashed lines. [Symmetry codes: (i) x, 1/2 - y, z + 1/2; (ii) x - 1, y, z; (iii) 1 - x, 1/2 - y, z + 1/2].
3-(5-Chloro-2-hydroxy-5-chloroanilino)isobenzofuran-1(3H)-one top
Crystal data top
C14H10ClNO3F(000) = 568
Mr = 275.68Dx = 1.502 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11707 reflections
a = 9.0439 (6) Åθ = 2.4–27.9°
b = 11.5363 (10) ŵ = 0.32 mm1
c = 12.6602 (9) ÅT = 296 K
β = 112.593 (5)°Plate, colourless
V = 1219.51 (16) Å30.53 × 0.39 × 0.13 mm
Z = 4
Data collection top
Stoe IPDS 2
diffractometer
2392 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1898 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.134
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.4°
ω scansh = 1111
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1414
Tmin = 0.731, Tmax = 0.955l = 1515
11707 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)] = 0.053All 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 reflectionsΔρmax = 0.32 e Å3
213 parametersΔρmin = 0.37 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: 0.008 (1)
Crystal data top
C14H10ClNO3V = 1219.51 (16) Å3
Mr = 275.68Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.0439 (6) ŵ = 0.32 mm1
b = 11.5363 (10) ÅT = 296 K
c = 12.6602 (9) Å0.53 × 0.39 × 0.13 mm
β = 112.593 (5)°
Data collection top
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 = 0.955Rint = 0.134
11707 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.147All H-atom parameters refined
S = 1.03Δρmax = 0.32 e Å3
2392 reflectionsΔρmin = 0.37 e Å3
213 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
C10.4753 (3)0.2984 (2)0.3612 (2)0.0528 (5)
C20.5622 (3)0.34482 (18)0.4771 (2)0.0492 (5)
C30.5358 (3)0.3266 (2)0.5766 (2)0.0584 (6)
C40.6373 (4)0.3805 (2)0.6741 (2)0.0619 (6)
C50.7624 (3)0.4495 (2)0.6728 (2)0.0620 (6)
C60.7886 (3)0.4667 (2)0.5734 (2)0.0598 (6)
C70.6855 (3)0.41331 (19)0.4756 (2)0.0491 (5)
C80.6824 (3)0.4165 (2)0.3563 (2)0.0520 (5)
C90.8505 (3)0.37712 (19)0.2471 (2)0.0495 (5)
C100.9761 (3)0.3099 (2)0.2418 (2)0.0534 (5)
C111.0103 (3)0.3104 (2)0.1448 (2)0.0578 (6)
C120.9220 (3)0.3779 (2)0.0514 (2)0.0575 (6)
C130.7988 (3)0.4440 (2)0.0573 (2)0.0545 (5)
C140.7618 (3)0.4443 (2)0.1535 (2)0.0535 (6)
N10.8247 (2)0.37584 (19)0.34941 (19)0.0557 (5)
O10.3639 (2)0.23271 (17)0.32605 (17)0.0680 (5)
O20.54328 (19)0.34162 (16)0.29172 (15)0.0578 (4)
O31.0593 (2)0.24668 (18)0.33773 (18)0.0673 (5)
Cl10.68573 (8)0.53075 (6)0.05833 (6)0.0703 (3)
H10.679 (3)0.489 (2)0.154 (2)0.051 (6)*
H21.091 (3)0.264 (2)0.141 (2)0.056 (7)*
H30.449 (3)0.279 (3)0.578 (2)0.072 (8)*
H40.654 (3)0.492 (2)0.320 (2)0.058 (7)*
H50.829 (3)0.485 (2)0.740 (2)0.063 (7)*
H60.873 (3)0.514 (2)0.575 (2)0.063 (7)*
H70.949 (3)0.383 (2)0.017 (3)0.071 (8)*
H80.626 (4)0.371 (3)0.743 (3)0.086 (10)*
H90.864 (3)0.320 (2)0.390 (2)0.052 (7)*
H101.147 (4)0.226 (3)0.339 (3)0.097 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0449 (11)0.0537 (12)0.0662 (14)0.0042 (10)0.0283 (10)0.0003 (10)
C20.0474 (11)0.0472 (11)0.0587 (13)0.0058 (9)0.0268 (10)0.0013 (9)
C30.0639 (14)0.0550 (13)0.0691 (15)0.0014 (11)0.0398 (13)0.0052 (11)
C40.0826 (17)0.0532 (13)0.0594 (15)0.0075 (12)0.0377 (13)0.0042 (11)
C50.0720 (15)0.0554 (13)0.0582 (14)0.0000 (12)0.0245 (12)0.0059 (11)
C60.0613 (14)0.0575 (13)0.0662 (15)0.0063 (11)0.0307 (12)0.0043 (11)
C70.0480 (11)0.0468 (11)0.0584 (13)0.0054 (9)0.0269 (10)0.0009 (9)
C80.0495 (11)0.0543 (12)0.0596 (13)0.0001 (10)0.0291 (10)0.0017 (10)
C90.0439 (11)0.0518 (11)0.0601 (13)0.0067 (9)0.0283 (10)0.0028 (10)
C100.0464 (11)0.0512 (12)0.0687 (14)0.0044 (9)0.0288 (11)0.0000 (10)
C110.0545 (13)0.0537 (12)0.0776 (16)0.0004 (10)0.0391 (12)0.0062 (11)
C120.0589 (13)0.0596 (13)0.0647 (15)0.0096 (11)0.0358 (12)0.0084 (11)
C130.0520 (12)0.0570 (12)0.0581 (13)0.0087 (10)0.0253 (10)0.0030 (10)
C140.0450 (11)0.0577 (12)0.0644 (14)0.0008 (10)0.0286 (10)0.0016 (11)
N10.0490 (10)0.0636 (12)0.0632 (12)0.0065 (9)0.0310 (9)0.0081 (10)
O10.0509 (9)0.0766 (11)0.0786 (13)0.0112 (8)0.0274 (9)0.0126 (9)
O20.0494 (8)0.0721 (10)0.0587 (10)0.0012 (7)0.0282 (7)0.0063 (8)
O30.0554 (10)0.0744 (11)0.0813 (13)0.0143 (9)0.0366 (9)0.0147 (9)
Cl10.0659 (4)0.0854 (5)0.0623 (4)0.0049 (3)0.0278 (3)0.0081 (3)
Geometric parameters (Å, º) top
C1—O11.201 (3)C8—H40.98 (3)
C1—O21.348 (3)C9—C141.386 (3)
C1—C21.474 (3)C9—C101.398 (3)
C2—C71.373 (3)C9—N11.401 (3)
C2—C31.385 (3)C10—O31.368 (3)
C3—C41.373 (4)C10—C111.376 (4)
C3—H30.96 (3)C11—C121.385 (4)
C4—C51.388 (4)C11—H20.92 (3)
C4—H80.93 (4)C12—C131.374 (3)
C5—C61.382 (4)C12—H70.98 (3)
C5—H50.93 (3)C13—C141.381 (3)
C6—C71.377 (3)C13—Cl11.744 (3)
C6—H60.94 (3)C14—H10.92 (3)
C7—C81.500 (3)N1—H90.82 (3)
C8—N11.404 (3)O3—H100.83 (4)
C8—O21.486 (3)
O1—C1—O2121.3 (2)O2—C8—H4104.3 (15)
O1—C1—C2130.5 (2)C7—C8—H4113.7 (16)
O2—C1—C2108.22 (19)C14—C9—C10118.9 (2)
C7—C2—C3121.7 (2)C14—C9—N1123.3 (2)
C7—C2—C1108.7 (2)C10—C9—N1117.8 (2)
C3—C2—C1129.6 (2)O3—C10—C11124.0 (2)
C4—C3—C2117.4 (2)O3—C10—C9115.6 (2)
C4—C3—H3120.6 (18)C11—C10—C9120.4 (2)
C2—C3—H3122.1 (18)C10—C11—C12120.7 (2)
C3—C4—C5121.0 (2)C10—C11—H2119.8 (16)
C3—C4—H8121 (2)C12—C11—H2119.5 (16)
C5—C4—H8118 (2)C13—C12—C11118.6 (2)
C6—C5—C4121.3 (3)C13—C12—H7119.5 (17)
C6—C5—H5119.6 (18)C11—C12—H7121.8 (17)
C4—C5—H5119.1 (18)C12—C13—C14121.7 (2)
C7—C6—C5117.5 (2)C12—C13—Cl1119.92 (19)
C7—C6—H6122.8 (18)C14—C13—Cl1118.39 (19)
C5—C6—H6119.7 (18)C13—C14—C9119.7 (2)
C2—C7—C6121.2 (2)C13—C14—H1119.2 (16)
C2—C7—C8109.1 (2)C9—C14—H1121.1 (16)
C6—C7—C8129.7 (2)C9—N1—C8122.4 (2)
N1—C8—O2111.98 (19)C9—N1—H9114.0 (19)
N1—C8—C7113.0 (2)C8—N1—H9114.4 (19)
O2—C8—C7102.92 (18)C1—O2—C8111.01 (18)
N1—C8—H4110.4 (16)C10—O3—H10111 (3)
O1—C1—C2—C7177.5 (2)N1—C9—C10—O31.6 (3)
O2—C1—C2—C71.8 (2)C14—C9—C10—C110.3 (3)
O1—C1—C2—C31.5 (4)N1—C9—C10—C11178.0 (2)
O2—C1—C2—C3179.2 (2)O3—C10—C11—C12179.1 (2)
C7—C2—C3—C40.5 (3)C9—C10—C11—C120.5 (4)
C1—C2—C3—C4179.4 (2)C10—C11—C12—C130.4 (4)
C2—C3—C4—C50.7 (4)C11—C12—C13—C140.0 (4)
C3—C4—C5—C60.3 (4)C11—C12—C13—Cl1179.65 (18)
C4—C5—C6—C70.3 (4)C12—C13—C14—C90.2 (4)
C3—C2—C7—C60.2 (3)Cl1—C13—C14—C9179.39 (17)
C1—C2—C7—C6179.0 (2)C10—C9—C14—C130.1 (3)
C3—C2—C7—C8179.8 (2)N1—C9—C14—C13177.5 (2)
C1—C2—C7—C81.1 (2)C14—C9—N1—C817.8 (4)
C5—C6—C7—C20.6 (4)C10—C9—N1—C8164.5 (2)
C5—C6—C7—C8179.3 (2)O2—C8—N1—C967.8 (3)
C2—C7—C8—N1121.1 (2)C7—C8—N1—C9176.5 (2)
C6—C7—C8—N159.0 (3)O1—C1—O2—C8177.6 (2)
C2—C7—C8—O20.1 (2)C2—C1—O2—C81.7 (2)
C6—C7—C8—O2180.0 (2)N1—C8—O2—C1120.7 (2)
C14—C9—C10—O3179.4 (2)C7—C8—O2—C11.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H10···O1i0.83 (4)2.03 (4)2.820 (3)160
C11—H2···O1i0.92 (3)2.70 (3)3.265 (3)121
C4—H8···O2ii0.92 (4)2.70 (4)3.237 (3)117
C5—H5···Cg1iii0.93 (2)2.8853.695 (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 formulaC14H10ClNO3
Mr275.68
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.0439 (6), 11.5363 (10), 12.6602 (9)
β (°) 112.593 (5)
V3)1219.51 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.53 × 0.39 × 0.13
Data collection
DiffractometerStoe IPDS 2
Absorption correctionIntegration
(X-RED; Stoe & Cie, 2002)
Tmin, Tmax0.731, 0.955
No. of measured, independent and
observed [I > 2σ(I)] reflections
11707, 2392, 1898
Rint0.134
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.147, 1.03
No. of reflections2392
No. of parameters213
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H10···O1i0.83 (4)2.03 (4)2.820 (3)160
C11—H2···O1i0.92 (3)2.70 (3)3.265 (3)121
C4—H8···O2ii0.92 (4)2.70 (4)3.237 (3)117
C5—H5···Cg1iii0.93 (2)2.8853.695 (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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