Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680800754X/hk2434sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680800754X/hk2434Isup2.hkl
Contains datablock I

CCDC reference: 684549

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.093
  • Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C SHFSU01_ALERT_2_C Test not performed. _refine_ls_shift/su_max and _refine_ls_shift/esd_max not present. Absolute value of the parameter shift to su ratio given 0.001
Alert level G PLAT793_ALERT_2_G Check the Absolute Configuration of C8 ..... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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 m3
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 mm1
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 = 99
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2828
Tmin = 0.958, Tmax = 0.982l = 88
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 Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C15H11NO4V = 1229.88 (14) Å3
Mr = 269.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8135 (6) ŵ = 0.11 mm1
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 Å3
2536 reflectionsΔρmin = 0.17 e Å3
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—C81.67 (18)C7—C8—O2—C13.01 (18)
O1—C1—C2—C7179.60 (18)O2—C8—N1—C972.79 (19)
O2—C1—C2—C70.52 (19)C7—C8—N1—C9169.91 (14)
O1—C1—C2—C32.1 (3)C14—C9—N1—C84.3 (2)
O2—C1—C2—C3177.00 (17)C10—C9—N1—C8174.57 (15)
C7—C2—C3—C40.0 (3)N1—C9—C10—C11177.90 (15)
C1—C2—C3—C4177.23 (17)C14—C9—C10—C111.0 (2)
C2—C3—C4—C50.1 (3)N1—C9—C10—C151.1 (2)
C3—C4—C5—C60.1 (3)C14—C9—C10—C15179.97 (15)
C4—C5—C6—C70.0 (3)C9—C10—C11—C121.2 (2)
C5—C6—C7—C20.1 (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—C140.4 (3)
C1—C2—C7—C6177.86 (16)C12—C13—C14—C90.3 (3)
C3—C2—C7—C8175.31 (16)N1—C9—C14—C13178.36 (16)
C1—C2—C7—C82.45 (19)C10—C9—C14—C130.5 (2)
C6—C7—C8—N160.0 (3)C11—C10—C15—O3177.61 (16)
C2—C7—C8—N1125.16 (15)C9—C10—C15—O33.4 (2)
C6—C7—C8—O2178.07 (18)C11—C10—C15—O41.8 (2)
C2—C7—C8—O23.27 (18)C9—C10—C15—O4177.24 (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, z1/2.

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)
V3)1229.88 (14)
Z4
Radiation typeMo Kα
µ (mm1)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)max1)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 Å3)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, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds