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The title compound, C14H11NO3, is stabilized by inter­molecular O—H...O, N—H...O and C—H...O hydrogen bonds, and by three C—H...π inter­molecular inter­actions. The N—H...O and O—H...O hydrogen bonds generate edge-fused R44(26) rings. The phthalide ring system of the mol­ecule is almost planar and forms a dihedral angle of 63.02 (7)° with the second benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013031/rz2022sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013031/rz2022Isup2.hkl
Contains datablock I

CCDC reference: 608477

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.067
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.04 PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. CG2 .. 3.00 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. CG1 .. 3.05 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 1183 Count of symmetry unique reflns 1183 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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

Computing details top

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-Hydroxyanilino)isobenzofuran-1(3H)-one top
Crystal data top
C14H11NO3F(000) = 504
Mr = 241.24Dx = 1.337 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 8507 reflections
a = 5.9049 (4) Åθ = 2.3–27.9°
b = 17.4841 (16) ŵ = 0.10 mm1
c = 11.7553 (8) ÅT = 296 K
β = 99.113 (6)°Prism, brown
V = 1198.32 (16) Å30.60 × 0.52 × 0.39 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
1183 independent reflections
Radiation source: fine-focus sealed tube1138 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.031
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 77
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2121
Tmin = 0.940, Tmax = 0.971l = 1413
8507 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)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0458P)2 + 0.0931P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1183 reflectionsΔρmax = 0.10 e Å3
168 parametersΔρmin = 0.10 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.025 (4)
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
C20.7404 (3)0.21598 (10)0.77051 (15)0.0505 (4)
C30.7108 (4)0.14830 (11)0.82690 (17)0.0623 (5)
H30.81860.13140.88810.075*
C40.5157 (4)0.10686 (11)0.78886 (18)0.0656 (5)
H40.49070.06090.82460.079*
C50.3574 (4)0.13247 (12)0.6988 (2)0.0673 (5)
H50.22560.10380.67560.081*
C60.3886 (4)0.19968 (11)0.64171 (17)0.0606 (5)
H60.28090.21640.58040.073*
C70.5853 (3)0.24110 (10)0.67888 (14)0.0491 (4)
C80.6642 (3)0.31580 (10)0.63582 (16)0.0535 (4)
H80.69680.30930.55720.064*
C10.9226 (3)0.27263 (10)0.79504 (16)0.0565 (4)
C90.5097 (3)0.44376 (9)0.57864 (13)0.0479 (4)
C100.3316 (3)0.49488 (11)0.58353 (16)0.0544 (4)
H100.22270.48390.63030.065*
C110.3133 (3)0.56159 (11)0.52034 (16)0.0545 (4)
H110.19360.59540.52520.065*
C120.4730 (3)0.57820 (10)0.44964 (14)0.0501 (4)
C130.6518 (3)0.52839 (10)0.44534 (16)0.0560 (4)
H130.76040.53950.39840.067*
C140.6720 (3)0.46212 (10)0.50985 (16)0.0541 (4)
H140.79550.42950.50720.065*
N10.5067 (3)0.37439 (9)0.63805 (15)0.0611 (4)
O11.0857 (3)0.27155 (9)0.87252 (13)0.0753 (5)
O20.8869 (2)0.32913 (7)0.71767 (12)0.0613 (4)
O30.4655 (3)0.64365 (8)0.38537 (13)0.0697 (4)
H3A0.35250.66880.39440.105*
H10.438 (5)0.3753 (13)0.697 (2)0.068 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0582 (10)0.0468 (8)0.0457 (8)0.0047 (7)0.0052 (7)0.0019 (7)
C30.0740 (12)0.0549 (10)0.0553 (10)0.0040 (9)0.0023 (9)0.0098 (8)
C40.0821 (13)0.0523 (10)0.0639 (11)0.0158 (9)0.0161 (10)0.0033 (9)
C50.0686 (12)0.0650 (11)0.0689 (12)0.0217 (10)0.0131 (10)0.0116 (10)
C60.0597 (10)0.0630 (10)0.0558 (10)0.0072 (9)0.0011 (8)0.0053 (8)
C70.0598 (9)0.0432 (8)0.0438 (8)0.0003 (7)0.0073 (7)0.0034 (6)
C80.0671 (10)0.0458 (8)0.0481 (8)0.0003 (7)0.0106 (8)0.0015 (8)
C10.0637 (10)0.0522 (9)0.0526 (10)0.0107 (8)0.0060 (8)0.0015 (8)
C90.0566 (9)0.0440 (8)0.0430 (8)0.0001 (7)0.0074 (7)0.0021 (7)
C100.0526 (9)0.0576 (9)0.0563 (9)0.0001 (7)0.0186 (7)0.0004 (8)
C110.0507 (8)0.0565 (10)0.0575 (10)0.0119 (7)0.0127 (7)0.0008 (8)
C120.0559 (9)0.0501 (8)0.0448 (8)0.0065 (7)0.0090 (7)0.0036 (7)
C130.0588 (10)0.0541 (9)0.0596 (10)0.0087 (8)0.0230 (8)0.0071 (8)
C140.0545 (9)0.0507 (8)0.0595 (10)0.0121 (8)0.0166 (8)0.0047 (8)
N10.0809 (11)0.0499 (8)0.0576 (9)0.0079 (8)0.0264 (8)0.0066 (7)
O10.0703 (9)0.0830 (10)0.0655 (8)0.0245 (8)0.0106 (7)0.0037 (7)
O20.0705 (8)0.0505 (7)0.0626 (8)0.0137 (6)0.0093 (6)0.0016 (6)
O30.0829 (9)0.0621 (9)0.0700 (8)0.0252 (7)0.0296 (7)0.0226 (7)
Geometric parameters (Å, º) top
C2—C71.371 (2)C1—O21.337 (2)
C2—C31.381 (3)C9—C141.386 (2)
C2—C11.457 (2)C9—C101.388 (2)
C3—C41.375 (3)C9—N11.401 (2)
C3—H30.9300C10—C111.378 (3)
C4—C51.371 (3)C10—H100.9300
C4—H40.9300C11—C121.383 (3)
C5—C61.380 (3)C11—H110.9300
C5—H50.9300C12—O31.368 (2)
C6—C71.380 (3)C12—C131.376 (2)
C6—H60.9300C13—C141.380 (2)
C7—C81.501 (2)C13—H130.9300
C8—N11.387 (2)C14—H140.9300
C8—O21.519 (2)N1—H10.85 (3)
C8—H80.9800O3—H3A0.8200
C1—O11.216 (2)
C7—C2—C3122.13 (17)O1—C1—C2127.58 (17)
C7—C2—C1108.56 (15)O2—C1—C2109.62 (16)
C3—C2—C1129.28 (17)C14—C9—C10118.27 (15)
C4—C3—C2117.32 (18)C14—C9—N1123.76 (15)
C4—C3—H3121.3C10—C9—N1117.85 (15)
C2—C3—H3121.3C11—C10—C9121.19 (16)
C5—C4—C3120.83 (18)C11—C10—H10119.4
C5—C4—H4119.6C9—C10—H10119.4
C3—C4—H4119.6C10—C11—C12119.93 (16)
C4—C5—C6121.76 (18)C10—C11—H11120.0
C4—C5—H5119.1C12—C11—H11120.0
C6—C5—H5119.1O3—C12—C13117.86 (15)
C7—C6—C5117.60 (18)O3—C12—C11122.80 (16)
C7—C6—H6121.2C13—C12—C11119.31 (16)
C5—C6—H6121.2C12—C13—C14120.76 (15)
C2—C7—C6120.33 (17)C12—C13—H13119.6
C2—C7—C8109.81 (16)C14—C13—H13119.6
C6—C7—C8129.84 (17)C13—C14—C9120.51 (15)
N1—C8—C7113.02 (17)C13—C14—H14119.7
N1—C8—O2113.01 (15)C9—C14—H14119.7
C7—C8—O2101.75 (14)C8—N1—C9124.65 (16)
N1—C8—H8109.6C8—N1—H1115.8 (16)
C7—C8—H8109.6C9—N1—H1115.6 (16)
O2—C8—H8109.6C1—O2—C8110.18 (13)
O1—C1—O2122.81 (17)C12—O3—H3A109.5
C7—C2—C3—C41.1 (3)C14—C9—C10—C111.1 (3)
C1—C2—C3—C4176.9 (2)N1—C9—C10—C11175.00 (17)
C2—C3—C4—C50.3 (3)C9—C10—C11—C120.6 (3)
C3—C4—C5—C61.1 (3)C10—C11—C12—O3179.52 (17)
C4—C5—C6—C70.5 (3)C10—C11—C12—C131.4 (3)
C3—C2—C7—C61.7 (3)O3—C12—C13—C14178.72 (16)
C1—C2—C7—C6176.61 (17)C11—C12—C13—C140.5 (3)
C3—C2—C7—C8179.83 (18)C12—C13—C14—C91.2 (3)
C1—C2—C7—C81.8 (2)C10—C9—C14—C132.0 (3)
C5—C6—C7—C20.9 (3)N1—C9—C14—C13173.85 (16)
C5—C6—C7—C8179.01 (19)C7—C8—N1—C9164.02 (16)
C2—C7—C8—N1121.78 (18)O2—C8—N1—C981.1 (2)
C6—C7—C8—N156.5 (3)C14—C9—N1—C80.1 (3)
C2—C7—C8—O20.31 (18)C10—C9—N1—C8175.98 (18)
C6—C7—C8—O2177.94 (18)O1—C1—O2—C8177.37 (19)
C7—C2—C1—O1177.2 (2)C2—C1—O2—C82.64 (19)
C3—C2—C1—O11.0 (3)N1—C8—O2—C1120.02 (17)
C7—C2—C1—O22.8 (2)C7—C8—O2—C11.47 (17)
C3—C2—C1—O2178.97 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1i0.821.872.673 (2)165
N1—H1···O3ii0.85 (3)2.23 (3)2.972 (2)147 (2)
C8—H8···O1iii0.982.593.417 (2)143
C3—H3···Cg2iv0.933.003.777 (2)142
C5—H5···Cg2v0.932.703.513 (2)147
C11—H11···Cg1vi0.933.053.722 (2)130
Symmetry codes: (i) x1, y+1, z1/2; (ii) x, y+1, z+1/2; (iii) x1/2, y+1/2, z1/2; (iv) x+1/2, y+1/2, z+1/2; (v) x1/2, y+1/2, z; (vi) x1/2, y1/2, z.
 

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