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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 4| April 2008| Pages o752-o753
doi:10.1107/S160053680800754X

2-(3-Oxo-1,3-di­hydro­isobenzo­furan-1-ylamino)benzoic acid†

Mustafa Odabaşoğlua and Orhan Büyükgüngörb*

aDepartment of Chemistry, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, and bDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
*Correspondence e-mail: orhanb@omu.edu.tr

(Received 19 March 2008; accepted 19 March 2008; online 29 March 2008)

In the mol­ecule of the title compound, C15H11NO4, the essentially planar phthalide group is oriented at a dihedral angle of 56.78 (5)° with respect to the substituted aromatic ring. An intra­molecular N—H⋯O hydrogen bond results in the formation of a non-planar six-membered ring, which adopts a nearly flattened-boat conformation. In the crystal structure, inter­molecular C—H⋯O, O—H⋯O and N—H⋯O hydrogen bonds link the mol­ecules, generating centrosymmetric R22(8) and R22(11) ring motifs and forming a three-dimensional network.

Related literature

For general background, see: Aoki et al. (1973[Aoki, K., Furusho, T., Kimura, T., Satake, K. & Funayama, S. (1973). Jpn Patent No. 7 324 724;.], 1974[Aoki, K., Furusho, T., Kimura, T., Satake, K. & Funayama, S. (1974). Chem. Abstr. 80, 129246.]); Lacova (1973[Lacova, M. (1973). Chem. Zvesti, 27, 525-535.], 1974[Lacova, M. (1974). Chem. Abstr. 80, 59757.]); Elderfield (1951[Elderfield, R. C. (1951). Heterocylic Compounds, Vol. 2, ch. 2. New York: Wiley.]); Bellasio (1974[Bellasio, E. (1974). Ger. Patent No. 2 422 193.], 1975[Bellasio, E. (1975). Chem. Abstr. 83, 9788.]); Roy & Sarkar (2005[Roy, H. N. & Sarkar, M. S. (2005). Synth. Commun. 35, 2177-2181.]); Kubota & Tatsuno (1971[Kubota, Y. & Tatsuno, T. (1971). Chem. Pharm. Bull. 19, 1226-1233.]); Tsi & Tan (1997[Tsi, D. & Tan, B. K. H. (1997). Phytother. Res. 11, 576-582.]). For related structures, see: Büyükgüngör & Odabaşoğlu (2006[Büyükgüngör, O. & Odabaşoğlu, M. (2006). Acta Cryst. E62, o2936-o2937.]); Odabaşoğlu & Büyükgüngör (2006[Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1879-o1881.]; 2007[Odabaşoğlu, M. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4730.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For ring motif details, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data

  • C15H11NO4

  • Mr = 269.25

  • Monoclinic, P 21 /c

  • a = 7.8135 (6) Å

  • b = 22.6205 (10) Å

  • c = 7.0902 (5) Å

  • β = 101.061 (5)°

  • V = 1229.88 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 296 K

  • 0.55 × 0.36 × 0.18 mm
Data collection

  • Stoe IPDS II diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.958, Tmax = 0.982

  • 12715 measured reflections

  • 2536 independent reflections

  • 1958 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.093

  • S = 1.07

  • 2536 reflections

  • 225 parameters

  • All H-atom parameters refined

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O3 0.86 (2) 2.074 (19) 2.7004 (18) 129.3 (16)
N1—H1⋯O1i 0.86 (2) 2.58 (2) 3.281 (2) 138.9 (15)
O4—H4A⋯O3ii 0.97 (3) 1.67 (3) 2.6329 (17) 174 (2)
C4—H4⋯O2iii 0.93 (2) 2.58 (2) 3.464 (2) 158.9 (17)
C8—H8⋯O1iv 0.983 (18) 2.580 (17) 3.403 (2) 141.4 (12)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+2; (iii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800754X/hk2434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800754X/hk2434Isup2.hkl

checkCIF report


Comment top

Phthalides are known to show diverse biological activities as hormones, pheromones and antibiotics (Aoki et al., 1973, 1974; Lacova, 1973, 1974; Elderfield, 1951; Bellasio, 1974, 1975; Roy & Sarkar, 2005; Kubota & Tatsuno, 1971; Tsi & Tan, 1997). As part of our ongoing research on 3-substituted phthalides (Büyükgüngör & Odabaşoğlu, 2006; Odabaşoğlu & Büyükgüngör, 2006; 2007), the title compound, (I), has been synthesized and its crystal structure is reported here.

In the molecule of (I), (Fig. 1), rings A (C2-C7), B (C1/C2/C7/C8/O2) and C (C9-C14) are, of course, planar. The dihedral angles between them are A/B = 3.08 (3)°, A/C = 57.11 (4)° and B/C = 56.56 (5)°. So, rings A and B are also nearly coplanar. Ring C is oriented with respect to the coplanar ring system at a dihedral angle of 56.78 (5)°. The intramolecular N-H···O hydrogen bond (Table 1) results in the formation of a non-planar six-membered ring D (N1/H1/O3/C9/C10/C15), having total puckering amplitude, QT, of 1.408 (3) Å, in which it adopts a nearly flattened-boat [ϕ = -42.43 (2)° and θ = 97.94 (3)°] conformation (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O, O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules, generating centrosymmetric R22(8) and R22(11) (Fig. 2) ring motifs (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Aoki et al. (1973, 1974); Lacova (1973, 1974); Elderfield (1951); Bellasio (1974, 1975); Roy & Sarkar (2005); Kubota & Tatsuno (1971); Tsi & Tan (1997). For related structures, see: Büyükgüngör & Odabaşoğlu (2006); Odabaşoğlu & Büyükgüngör (2006; 2007). For ring puckering parameters, see: Cremer & Pople (1975). For ring motif details, see: Bernstein et al. (1995); Etter (1990).

Experimental top

The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006), using phthalaldehydic acid and antranilic acid as starting materials (yield; 70%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol-DMF (1:1) solution at room temperature.

Refinement top

H atoms were located in difference synthesis and refined freely [C-H = 0.93 (2)-0.983 (18) Å and Uiso(H) = 0.036 (4)-0.060 (6) Å2; N-H = 0.86 (2) Å and Uiso(H) = 0.046 (5) Å2; O-H = 0.97 (3) Å and Uiso(H) = 0.094 (9) Å2].

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line.
[Figure 2] Fig. 2. A partial packing diagram of (I), showing the formation of R22(8) and R22(11) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x, 1/2 - y, z - 1/2; (ii) 1 - x, -y, 2 - z]. H atoms not involved in hydrogen bondings have been omitted for clarity.
2-(3-oxo-1,3-dihydroisobenzofuran-1-ylamino)benzoic acid top
Crystal data top
C15H11NO4F(000) = 560
Mr = 269.25Dx = 1.454 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12715 reflections
a = 7.8135 (6) Åθ = 1.8–27.3°
b = 22.6205 (10) ŵ = 0.11 mm−1
c = 7.0902 (5) ÅT = 296 K
β = 101.061 (5)°Prism, colorless
V = 1229.88 (14) Å30.55 × 0.36 × 0.18 mm
Z = 4
Data collection top
Stoe IPDSII
diffractometer		2536 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1958 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.034
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 1.8°
ω scan rotation methodh = −9→9
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −28→28
Tmin = 0.958, Tmax = 0.982l = −8→8
12715 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.2251P]
where P = (Fo2 + 2Fc2)/3
2536 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C15H11NO4V = 1229.88 (14) Å3
Mr = 269.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8135 (6) ŵ = 0.11 mm−1
b = 22.6205 (10) ÅT = 296 K
c = 7.0902 (5) Å0.55 × 0.36 × 0.18 mm
β = 101.061 (5)°
Data collection top
Stoe IPDSII
diffractometer		2536 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		1958 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.982Rint = 0.034
12715 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.093All H-atom parameters refined
S = 1.07Δρmax = 0.16 e Å−3
2536 reflectionsΔρmin = −0.17 e Å−3
225 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 > 2sigma(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
C10.6576 (2)0.26649 (7)0.4899 (2)0.0402 (4)
C20.8303 (2)0.24430 (7)0.5812 (2)0.0367 (4)
C30.9781 (3)0.27532 (8)0.6650 (3)0.0457 (4)
C41.1272 (3)0.24364 (9)0.7337 (3)0.0518 (5)
C51.1279 (3)0.18248 (9)0.7191 (3)0.0511 (5)
C60.9805 (2)0.15141 (8)0.6356 (3)0.0460 (4)
C70.8308 (2)0.18333 (7)0.5662 (2)0.0354 (4)
C80.6571 (2)0.16362 (7)0.4548 (3)0.0364 (4)
C90.4218 (2)0.09230 (6)0.4534 (2)0.0332 (4)
C100.3436 (2)0.04653 (6)0.5436 (2)0.0321 (3)
C110.1982 (2)0.01723 (7)0.4399 (3)0.0396 (4)
C120.1264 (2)0.03208 (8)0.2541 (3)0.0458 (4)
C130.2021 (2)0.07689 (8)0.1666 (3)0.0435 (4)
C140.3465 (2)0.10673 (7)0.2628 (2)0.0389 (4)
C150.4117 (2)0.02788 (6)0.7427 (2)0.0334 (3)
N10.56924 (19)0.12145 (6)0.5475 (2)0.0387 (3)
O10.60404 (19)0.31643 (5)0.4713 (2)0.0563 (4)
O20.55684 (15)0.21973 (5)0.41990 (18)0.0437 (3)
O30.53512 (17)0.05196 (5)0.84778 (17)0.0457 (3)
O40.32808 (17)−0.01696 (5)0.80153 (19)0.0481 (3)
H10.596 (2)0.1184 (8)0.670 (3)0.046 (5)*
H30.975 (3)0.3188 (9)0.671 (3)0.058 (6)*
H41.229 (3)0.2630 (9)0.792 (3)0.060 (6)*
H4A0.383 (3)−0.0277 (11)0.931 (4)0.094 (9)*
H51.233 (3)0.1623 (8)0.764 (3)0.055 (6)*
H60.980 (3)0.1090 (9)0.626 (3)0.053 (5)*
H80.665 (2)0.1498 (7)0.325 (3)0.036 (4)*
H110.149 (2)−0.0136 (8)0.506 (3)0.045 (5)*
H120.030 (3)0.0113 (9)0.191 (3)0.055 (6)*
H130.154 (2)0.0893 (8)0.035 (3)0.049 (5)*
H140.394 (2)0.1377 (8)0.199 (3)0.047 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0518 (10)0.0365 (8)0.0337 (9)−0.0007 (7)0.0115 (8)0.0015 (6)
C20.0436 (9)0.0365 (8)0.0316 (8)−0.0055 (7)0.0113 (7)−0.0002 (6)
C30.0524 (11)0.0441 (10)0.0421 (10)−0.0141 (8)0.0130 (8)−0.0057 (8)
C40.0421 (11)0.0669 (12)0.0456 (11)−0.0212 (10)0.0068 (9)−0.0065 (9)
C50.0371 (10)0.0647 (12)0.0497 (11)0.0009 (9)0.0041 (9)0.0057 (9)
C60.0433 (10)0.0409 (9)0.0520 (11)0.0000 (8)0.0040 (8)0.0030 (8)
C70.0375 (9)0.0359 (8)0.0333 (9)−0.0051 (7)0.0080 (7)0.0024 (6)
C80.0389 (9)0.0318 (8)0.0373 (9)−0.0013 (7)0.0040 (7)0.0031 (6)
C90.0321 (8)0.0308 (7)0.0361 (9)0.0020 (6)0.0044 (7)−0.0020 (6)
C100.0298 (8)0.0316 (7)0.0351 (9)0.0028 (6)0.0066 (7)0.0001 (6)
C110.0329 (9)0.0422 (9)0.0429 (10)−0.0047 (7)0.0054 (7)−0.0011 (7)
C120.0366 (10)0.0522 (10)0.0448 (11)−0.0082 (8)−0.0017 (8)−0.0046 (8)
C130.0426 (10)0.0487 (10)0.0351 (10)0.0033 (8)−0.0025 (8)0.0010 (7)
C140.0400 (10)0.0378 (8)0.0375 (9)−0.0014 (7)0.0041 (7)0.0041 (7)
C150.0316 (8)0.0309 (7)0.0385 (9)−0.0003 (6)0.0089 (7)−0.0008 (6)
N10.0415 (8)0.0396 (7)0.0325 (8)−0.0098 (6)0.0010 (6)0.0048 (6)
O10.0735 (10)0.0368 (6)0.0577 (9)0.0114 (6)0.0107 (7)0.0040 (6)
O20.0425 (7)0.0373 (6)0.0479 (7)0.0009 (5)−0.0001 (6)0.0049 (5)
O30.0525 (8)0.0435 (6)0.0369 (7)−0.0141 (6)−0.0020 (6)0.0051 (5)
O40.0461 (7)0.0540 (7)0.0419 (7)−0.0159 (6)0.0028 (6)0.0113 (6)
Geometric parameters (Å, º) top
O4—H4A0.97 (3)C8—O21.4872 (18)
N1—H10.86 (2)C8—H80.983 (18)
C1—O11.203 (2)C9—N11.383 (2)
C1—O21.355 (2)C9—C141.405 (2)
C1—C21.469 (2)C9—C101.415 (2)
C2—C71.383 (2)C10—C111.397 (2)
C2—C31.384 (2)C10—C151.472 (2)
C3—C41.375 (3)C11—C121.371 (3)
C3—H30.98 (2)C11—H110.96 (2)
C4—C51.387 (3)C12—C131.380 (3)
C4—H40.93 (2)C12—H120.93 (2)
C5—C61.382 (3)C13—C141.378 (2)
C5—H50.94 (2)C13—H130.98 (2)
C6—C71.382 (2)C14—H140.948 (19)
C6—H60.963 (19)C15—O31.2271 (19)
C7—C81.501 (2)C15—O41.3168 (19)
C8—N11.409 (2)
C1—O2—C8110.76 (12)N1—C8—C7115.34 (14)
C15—O4—H4A109.6 (15)O2—C8—C7103.22 (12)
C9—N1—C8122.22 (14)N1—C8—H8110.1 (10)
C9—N1—H1118.1 (13)O2—C8—H8104.0 (10)
C8—N1—H1118.7 (13)C7—C8—H8111.9 (10)
O1—C1—O2121.82 (16)N1—C9—C14120.64 (15)
O1—C1—C2129.81 (16)N1—C9—C10121.49 (14)
O2—C1—C2108.36 (13)C14—C9—C10117.86 (14)
C7—C2—C3121.61 (16)C11—C10—C9119.13 (15)
C7—C2—C1108.84 (14)C11—C10—C15118.49 (14)
C3—C2—C1129.51 (15)C9—C10—C15122.37 (14)
C4—C3—C2117.92 (17)C12—C11—C10122.10 (16)
C4—C3—H3122.0 (12)C12—C11—H11121.2 (11)
C2—C3—H3120.0 (12)C10—C11—H11116.7 (11)
C3—C4—C5120.56 (18)C11—C12—C13118.70 (16)
C3—C4—H4120.3 (13)C11—C12—H12119.0 (12)
C5—C4—H4119.1 (13)C13—C12—H12122.3 (13)
C6—C5—C4121.62 (19)C14—C13—C12121.22 (17)
C6—C5—H5120.1 (12)C14—C13—H13117.3 (11)
C4—C5—H5118.3 (12)C12—C13—H13121.5 (11)
C5—C6—C7117.75 (17)C13—C14—C9120.98 (16)
C5—C6—H6122.0 (12)C13—C14—H14118.8 (11)
C7—C6—H6120.3 (12)C9—C14—H14120.2 (11)
C6—C7—C2120.54 (16)O3—C15—O4121.99 (15)
C6—C7—C8130.55 (15)O3—C15—C10123.52 (14)
C2—C7—C8108.71 (14)O4—C15—C10114.49 (13)
N1—C8—O2111.53 (14)
O1—C1—O2—C8177.50 (16)N1—C8—O2—C1127.43 (15)
C2—C1—O2—C8−1.67 (18)C7—C8—O2—C13.01 (18)
O1—C1—C2—C7−179.60 (18)O2—C8—N1—C972.79 (19)
O2—C1—C2—C7−0.52 (19)C7—C8—N1—C9−169.91 (14)
O1—C1—C2—C3−2.1 (3)C14—C9—N1—C8−4.3 (2)
O2—C1—C2—C3177.00 (17)C10—C9—N1—C8174.57 (15)
C7—C2—C3—C40.0 (3)N1—C9—C10—C11−177.90 (15)
C1—C2—C3—C4−177.23 (17)C14—C9—C10—C111.0 (2)
C2—C3—C4—C5−0.1 (3)N1—C9—C10—C151.1 (2)
C3—C4—C5—C60.1 (3)C14—C9—C10—C15−179.97 (15)
C4—C5—C6—C70.0 (3)C9—C10—C11—C12−1.2 (2)
C5—C6—C7—C2−0.1 (3)C15—C10—C11—C12179.71 (16)
C5—C6—C7—C8174.15 (19)C10—C11—C12—C130.9 (3)
C3—C2—C7—C60.1 (3)C11—C12—C13—C14−0.4 (3)
C1—C2—C7—C6177.86 (16)C12—C13—C14—C90.3 (3)
C3—C2—C7—C8−175.31 (16)N1—C9—C14—C13178.36 (16)
C1—C2—C7—C82.45 (19)C10—C9—C14—C13−0.5 (2)
C6—C7—C8—N160.0 (3)C11—C10—C15—O3−177.61 (16)
C2—C7—C8—N1−125.16 (15)C9—C10—C15—O33.4 (2)
C6—C7—C8—O2−178.07 (18)C11—C10—C15—O41.8 (2)
C2—C7—C8—O2−3.27 (18)C9—C10—C15—O4−177.24 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86 (2)2.074 (19)2.7004 (18)129.3 (16)
N1—H1···O1i0.86 (2)2.58 (2)3.281 (2)138.9 (15)
O4—H4A···O3ii0.97 (3)1.67 (3)2.6329 (17)174 (2)
C4—H4···O2iii0.93 (2)2.58 (2)3.464 (2)158.9 (17)
C8—H8···O1iv0.983 (18)2.580 (17)3.403 (2)141.4 (12)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+2; (iii) x+1, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC15H11NO4
Mr269.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)7.8135 (6), 22.6205 (10), 7.0902 (5)
β (°) 101.061 (5)
V (Å3)1229.88 (14)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.55 × 0.36 × 0.18
Data collection
DiffractometerStoe IPDSII
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.958, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections		12715, 2536, 1958
Rint0.034
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.093, 1.07
No. of reflections2536
No. of parameters225
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.16, −0.17

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86 (2)2.074 (19)2.7004 (18)129.3 (16)
N1—H1···O1i0.86 (2)2.58 (2)3.281 (2)138.9 (15)
O4—H4A···O3ii0.97 (3)1.67 (3)2.6329 (17)174 (2)
C4—H4···O2iii0.93 (2)2.58 (2)3.464 (2)158.9 (17)
C8—H8···O1iv0.983 (18)2.580 (17)3.403 (2)141.4 (12)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+2; (iii) x+1, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2.
 

Footnotes

†3-Substituted phthalides. Part XXXIII.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund).

References

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ISSN: 2056-9890
Volume 64| Part 4| April 2008| Pages o752-o753
doi:10.1107/S160053680800754X
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