





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680800754X/hk2434sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053680800754X/hk2434Isup2.hkl |
CCDC reference: 684549
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(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
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.
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].
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).
C15H11NO4 | F(000) = 560 |
Mr = 269.25 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12715 reflections |
a = 7.8135 (6) Å | θ = 1.8–27.3° |
b = 22.6205 (10) Å | µ = 0.11 mm−1 |
c = 7.0902 (5) Å | T = 296 K |
β = 101.061 (5)° | Prism, colorless |
V = 1229.88 (14) Å3 | 0.55 × 0.36 × 0.18 mm |
Z = 4 |
Stoe IPDSII diffractometer | 2536 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1958 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.034 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 1.8° |
ω scan rotation method | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −28→28 |
Tmin = 0.958, Tmax = 0.982 | l = −8→8 |
12715 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | All 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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C15H11NO4 | V = 1229.88 (14) Å3 |
Mr = 269.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.8135 (6) Å | µ = 0.11 mm−1 |
b = 22.6205 (10) Å | T = 296 K |
c = 7.0902 (5) Å | 0.55 × 0.36 × 0.18 mm |
β = 101.061 (5)° |
Stoe IPDSII diffractometer | 2536 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1958 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.982 | Rint = 0.034 |
12715 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.093 | All H-atom parameters refined |
S = 1.07 | Δρmax = 0.16 e Å−3 |
2536 reflections | Δρmin = −0.17 e Å−3 |
225 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 > 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6576 (2) | 0.26649 (7) | 0.4899 (2) | 0.0402 (4) | |
C2 | 0.8303 (2) | 0.24430 (7) | 0.5812 (2) | 0.0367 (4) | |
C3 | 0.9781 (3) | 0.27532 (8) | 0.6650 (3) | 0.0457 (4) | |
C4 | 1.1272 (3) | 0.24364 (9) | 0.7337 (3) | 0.0518 (5) | |
C5 | 1.1279 (3) | 0.18248 (9) | 0.7191 (3) | 0.0511 (5) | |
C6 | 0.9805 (2) | 0.15141 (8) | 0.6356 (3) | 0.0460 (4) | |
C7 | 0.8308 (2) | 0.18333 (7) | 0.5662 (2) | 0.0354 (4) | |
C8 | 0.6571 (2) | 0.16362 (7) | 0.4548 (3) | 0.0364 (4) | |
C9 | 0.4218 (2) | 0.09230 (6) | 0.4534 (2) | 0.0332 (4) | |
C10 | 0.3436 (2) | 0.04653 (6) | 0.5436 (2) | 0.0321 (3) | |
C11 | 0.1982 (2) | 0.01723 (7) | 0.4399 (3) | 0.0396 (4) | |
C12 | 0.1264 (2) | 0.03208 (8) | 0.2541 (3) | 0.0458 (4) | |
C13 | 0.2021 (2) | 0.07689 (8) | 0.1666 (3) | 0.0435 (4) | |
C14 | 0.3465 (2) | 0.10673 (7) | 0.2628 (2) | 0.0389 (4) | |
C15 | 0.4117 (2) | 0.02788 (6) | 0.7427 (2) | 0.0334 (3) | |
N1 | 0.56924 (19) | 0.12145 (6) | 0.5475 (2) | 0.0387 (3) | |
O1 | 0.60404 (19) | 0.31643 (5) | 0.4713 (2) | 0.0563 (4) | |
O2 | 0.55684 (15) | 0.21973 (5) | 0.41990 (18) | 0.0437 (3) | |
O3 | 0.53512 (17) | 0.05196 (5) | 0.84778 (17) | 0.0457 (3) | |
O4 | 0.32808 (17) | −0.01696 (5) | 0.80153 (19) | 0.0481 (3) | |
H1 | 0.596 (2) | 0.1184 (8) | 0.670 (3) | 0.046 (5)* | |
H3 | 0.975 (3) | 0.3188 (9) | 0.671 (3) | 0.058 (6)* | |
H4 | 1.229 (3) | 0.2630 (9) | 0.792 (3) | 0.060 (6)* | |
H4A | 0.383 (3) | −0.0277 (11) | 0.931 (4) | 0.094 (9)* | |
H5 | 1.233 (3) | 0.1623 (8) | 0.764 (3) | 0.055 (6)* | |
H6 | 0.980 (3) | 0.1090 (9) | 0.626 (3) | 0.053 (5)* | |
H8 | 0.665 (2) | 0.1498 (7) | 0.325 (3) | 0.036 (4)* | |
H11 | 0.149 (2) | −0.0136 (8) | 0.506 (3) | 0.045 (5)* | |
H12 | 0.030 (3) | 0.0113 (9) | 0.191 (3) | 0.055 (6)* | |
H13 | 0.154 (2) | 0.0893 (8) | 0.035 (3) | 0.049 (5)* | |
H14 | 0.394 (2) | 0.1377 (8) | 0.199 (3) | 0.047 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0518 (10) | 0.0365 (8) | 0.0337 (9) | −0.0007 (7) | 0.0115 (8) | 0.0015 (6) |
C2 | 0.0436 (9) | 0.0365 (8) | 0.0316 (8) | −0.0055 (7) | 0.0113 (7) | −0.0002 (6) |
C3 | 0.0524 (11) | 0.0441 (10) | 0.0421 (10) | −0.0141 (8) | 0.0130 (8) | −0.0057 (8) |
C4 | 0.0421 (11) | 0.0669 (12) | 0.0456 (11) | −0.0212 (10) | 0.0068 (9) | −0.0065 (9) |
C5 | 0.0371 (10) | 0.0647 (12) | 0.0497 (11) | 0.0009 (9) | 0.0041 (9) | 0.0057 (9) |
C6 | 0.0433 (10) | 0.0409 (9) | 0.0520 (11) | 0.0000 (8) | 0.0040 (8) | 0.0030 (8) |
C7 | 0.0375 (9) | 0.0359 (8) | 0.0333 (9) | −0.0051 (7) | 0.0080 (7) | 0.0024 (6) |
C8 | 0.0389 (9) | 0.0318 (8) | 0.0373 (9) | −0.0013 (7) | 0.0040 (7) | 0.0031 (6) |
C9 | 0.0321 (8) | 0.0308 (7) | 0.0361 (9) | 0.0020 (6) | 0.0044 (7) | −0.0020 (6) |
C10 | 0.0298 (8) | 0.0316 (7) | 0.0351 (9) | 0.0028 (6) | 0.0066 (7) | 0.0001 (6) |
C11 | 0.0329 (9) | 0.0422 (9) | 0.0429 (10) | −0.0047 (7) | 0.0054 (7) | −0.0011 (7) |
C12 | 0.0366 (10) | 0.0522 (10) | 0.0448 (11) | −0.0082 (8) | −0.0017 (8) | −0.0046 (8) |
C13 | 0.0426 (10) | 0.0487 (10) | 0.0351 (10) | 0.0033 (8) | −0.0025 (8) | 0.0010 (7) |
C14 | 0.0400 (10) | 0.0378 (8) | 0.0375 (9) | −0.0014 (7) | 0.0041 (7) | 0.0041 (7) |
C15 | 0.0316 (8) | 0.0309 (7) | 0.0385 (9) | −0.0003 (6) | 0.0089 (7) | −0.0008 (6) |
N1 | 0.0415 (8) | 0.0396 (7) | 0.0325 (8) | −0.0098 (6) | 0.0010 (6) | 0.0048 (6) |
O1 | 0.0735 (10) | 0.0368 (6) | 0.0577 (9) | 0.0114 (6) | 0.0107 (7) | 0.0040 (6) |
O2 | 0.0425 (7) | 0.0373 (6) | 0.0479 (7) | 0.0009 (5) | −0.0001 (6) | 0.0049 (5) |
O3 | 0.0525 (8) | 0.0435 (6) | 0.0369 (7) | −0.0141 (6) | −0.0020 (6) | 0.0051 (5) |
O4 | 0.0461 (7) | 0.0540 (7) | 0.0419 (7) | −0.0159 (6) | 0.0028 (6) | 0.0113 (6) |
O4—H4A | 0.97 (3) | C8—O2 | 1.4872 (18) |
N1—H1 | 0.86 (2) | C8—H8 | 0.983 (18) |
C1—O1 | 1.203 (2) | C9—N1 | 1.383 (2) |
C1—O2 | 1.355 (2) | C9—C14 | 1.405 (2) |
C1—C2 | 1.469 (2) | C9—C10 | 1.415 (2) |
C2—C7 | 1.383 (2) | C10—C11 | 1.397 (2) |
C2—C3 | 1.384 (2) | C10—C15 | 1.472 (2) |
C3—C4 | 1.375 (3) | C11—C12 | 1.371 (3) |
C3—H3 | 0.98 (2) | C11—H11 | 0.96 (2) |
C4—C5 | 1.387 (3) | C12—C13 | 1.380 (3) |
C4—H4 | 0.93 (2) | C12—H12 | 0.93 (2) |
C5—C6 | 1.382 (3) | C13—C14 | 1.378 (2) |
C5—H5 | 0.94 (2) | C13—H13 | 0.98 (2) |
C6—C7 | 1.382 (2) | C14—H14 | 0.948 (19) |
C6—H6 | 0.963 (19) | C15—O3 | 1.2271 (19) |
C7—C8 | 1.501 (2) | C15—O4 | 1.3168 (19) |
C8—N1 | 1.409 (2) | ||
C1—O2—C8 | 110.76 (12) | N1—C8—C7 | 115.34 (14) |
C15—O4—H4A | 109.6 (15) | O2—C8—C7 | 103.22 (12) |
C9—N1—C8 | 122.22 (14) | N1—C8—H8 | 110.1 (10) |
C9—N1—H1 | 118.1 (13) | O2—C8—H8 | 104.0 (10) |
C8—N1—H1 | 118.7 (13) | C7—C8—H8 | 111.9 (10) |
O1—C1—O2 | 121.82 (16) | N1—C9—C14 | 120.64 (15) |
O1—C1—C2 | 129.81 (16) | N1—C9—C10 | 121.49 (14) |
O2—C1—C2 | 108.36 (13) | C14—C9—C10 | 117.86 (14) |
C7—C2—C3 | 121.61 (16) | C11—C10—C9 | 119.13 (15) |
C7—C2—C1 | 108.84 (14) | C11—C10—C15 | 118.49 (14) |
C3—C2—C1 | 129.51 (15) | C9—C10—C15 | 122.37 (14) |
C4—C3—C2 | 117.92 (17) | C12—C11—C10 | 122.10 (16) |
C4—C3—H3 | 122.0 (12) | C12—C11—H11 | 121.2 (11) |
C2—C3—H3 | 120.0 (12) | C10—C11—H11 | 116.7 (11) |
C3—C4—C5 | 120.56 (18) | C11—C12—C13 | 118.70 (16) |
C3—C4—H4 | 120.3 (13) | C11—C12—H12 | 119.0 (12) |
C5—C4—H4 | 119.1 (13) | C13—C12—H12 | 122.3 (13) |
C6—C5—C4 | 121.62 (19) | C14—C13—C12 | 121.22 (17) |
C6—C5—H5 | 120.1 (12) | C14—C13—H13 | 117.3 (11) |
C4—C5—H5 | 118.3 (12) | C12—C13—H13 | 121.5 (11) |
C5—C6—C7 | 117.75 (17) | C13—C14—C9 | 120.98 (16) |
C5—C6—H6 | 122.0 (12) | C13—C14—H14 | 118.8 (11) |
C7—C6—H6 | 120.3 (12) | C9—C14—H14 | 120.2 (11) |
C6—C7—C2 | 120.54 (16) | O3—C15—O4 | 121.99 (15) |
C6—C7—C8 | 130.55 (15) | O3—C15—C10 | 123.52 (14) |
C2—C7—C8 | 108.71 (14) | O4—C15—C10 | 114.49 (13) |
N1—C8—O2 | 111.53 (14) | ||
O1—C1—O2—C8 | 177.50 (16) | N1—C8—O2—C1 | 127.43 (15) |
C2—C1—O2—C8 | −1.67 (18) | C7—C8—O2—C1 | 3.01 (18) |
O1—C1—C2—C7 | −179.60 (18) | O2—C8—N1—C9 | 72.79 (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—C3 | 177.00 (17) | C10—C9—N1—C8 | 174.57 (15) |
C7—C2—C3—C4 | 0.0 (3) | N1—C9—C10—C11 | −177.90 (15) |
C1—C2—C3—C4 | −177.23 (17) | C14—C9—C10—C11 | 1.0 (2) |
C2—C3—C4—C5 | −0.1 (3) | N1—C9—C10—C15 | 1.1 (2) |
C3—C4—C5—C6 | 0.1 (3) | C14—C9—C10—C15 | −179.97 (15) |
C4—C5—C6—C7 | 0.0 (3) | C9—C10—C11—C12 | −1.2 (2) |
C5—C6—C7—C2 | −0.1 (3) | C15—C10—C11—C12 | 179.71 (16) |
C5—C6—C7—C8 | 174.15 (19) | C10—C11—C12—C13 | 0.9 (3) |
C3—C2—C7—C6 | 0.1 (3) | C11—C12—C13—C14 | −0.4 (3) |
C1—C2—C7—C6 | 177.86 (16) | C12—C13—C14—C9 | 0.3 (3) |
C3—C2—C7—C8 | −175.31 (16) | N1—C9—C14—C13 | 178.36 (16) |
C1—C2—C7—C8 | 2.45 (19) | C10—C9—C14—C13 | −0.5 (2) |
C6—C7—C8—N1 | 60.0 (3) | C11—C10—C15—O3 | −177.61 (16) |
C2—C7—C8—N1 | −125.16 (15) | C9—C10—C15—O3 | 3.4 (2) |
C6—C7—C8—O2 | −178.07 (18) | C11—C10—C15—O4 | 1.8 (2) |
C2—C7—C8—O2 | −3.27 (18) | C9—C10—C15—O4 | −177.24 (14) |
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+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 formula | C15H11NO4 |
Mr | 269.25 |
Crystal system, space group | Monoclinic, 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) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.55 × 0.36 × 0.18 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.958, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12715, 2536, 1958 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.093, 1.07 |
No. of reflections | 2536 |
No. of parameters | 225 |
H-atom treatment | All 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).
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+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. |
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.