Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050908/bt2541sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050908/bt2541Isup2.hkl |
CCDC reference: 667404
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.078
- Data-to-parameter ratio = 7.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.11 PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C1 .. 2.94 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 26.00 From the CIF: _reflns_number_total 1421 Count of symmetry unique reflns 1421 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 2 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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared by the reaction of tetrafluorophthalic anhydride (1.10 g, 5 mmol) with 2-aminophenol (0.55 g, 5 mmol) in the presence of 4-methylbenzenesulfonic acid in refluxing acetic acid (30 ml). Pale yellow block-shaped single crystals were obtained by slow evaporation of an acetone solution at room temperature (yield 79.7%, m.p. 526–527 K).
H atoms were placed at calculated positions and refined in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O) for the hydroxyl H atom. In the absence of significant anomalous scattering effects, Friedel pairs were merged.
N-Substituted 2,3,4,5-tetrafluorophthalimides are an important class of compounds because of their interesting biological activities (Collin et al., 2001; Miyachi et al., 1997; Niwayama et al., 1996). They are intermediates for the synthesis of fluoroquinolone antibiotics (Cai et al., 2006).
The bond lengths and angles of the title compound are within normal ranges (Allen et al., 1987). The isoindole unit (atoms N1/C1—C8) is essentially planar, with maximum deviation of 0.0493 (21) Å for atom C8. The dihedral angle between the isoindole unit and the hydroxyphenyl ring is 56.88 (6)°, which is less than that found in 2-(2-hydroxyphenyl)isoindoline-1,3-dione [71.8 (2)°] (Li et al., 2007) and 4,5,6,7-tetrachloro-2-(2-hydroxyphenyl)isoindoline-1,3-dione [63.78 (5)°] (Fun et al., 2007). The crystal structure is stabilized by an intermolecular O—H···O hydrogen bond (Table 1).
For related literature, see: Allen et al. (1987); Cai et al. (2006); Collin et al. (2001); Fun et al. (2007); Li et al. (2007); Miyachi et al. (1997); Niwayama et al. (1996).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 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: SHELXL97 (Bruker, 2002).
Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30% probability level. |
C14H5F4NO3 | F(000) = 624 |
Mr = 311.19 | Dx = 1.678 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5027 reflections |
a = 7.1741 (14) Å | θ = 2.6–27.9° |
b = 8.5862 (17) Å | µ = 0.16 mm−1 |
c = 19.994 (4) Å | T = 295 K |
V = 1231.6 (4) Å3 | Block, pale yellow |
Z = 4 | 0.36 × 0.20 × 0.16 mm |
Bruker APEX area-detector diffractometer | 1421 independent reflections |
Radiation source: fine-focus sealed tube | 1357 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −8→8 |
Tmin = 0.945, Tmax = 0.970 | k = −10→10 |
9661 measured reflections | l = −24→24 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0461P)2 + 0.1954P] where P = (Fo2 + 2Fc2)/3 |
1421 reflections | (Δ/σ)max = 0.001 |
200 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C14H5F4NO3 | V = 1231.6 (4) Å3 |
Mr = 311.19 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.1741 (14) Å | µ = 0.16 mm−1 |
b = 8.5862 (17) Å | T = 295 K |
c = 19.994 (4) Å | 0.36 × 0.20 × 0.16 mm |
Bruker APEX area-detector diffractometer | 1421 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1357 reflections with I > 2σ(I) |
Tmin = 0.945, Tmax = 0.970 | Rint = 0.022 |
9661 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.15 e Å−3 |
1421 reflections | Δρmin = −0.16 e Å−3 |
200 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 > 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. |
x | y | z | Uiso*/Ueq | ||
O2 | −0.1913 (2) | 0.8342 (2) | 1.01130 (8) | 0.0506 (4) | |
C1 | 0.2077 (3) | 0.9716 (2) | 0.93266 (10) | 0.0323 (4) | |
O1 | 0.30879 (19) | 0.9848 (2) | 0.88482 (7) | 0.0418 (4) | |
C2 | 0.2369 (3) | 1.0283 (2) | 1.00242 (10) | 0.0331 (4) | |
C3 | 0.3795 (3) | 1.1116 (3) | 1.02994 (11) | 0.0376 (5) | |
C4 | 0.3656 (3) | 1.1581 (3) | 1.09631 (12) | 0.0433 (5) | |
C5 | 0.2105 (4) | 1.1218 (3) | 1.13324 (11) | 0.0456 (5) | |
C6 | 0.0671 (3) | 1.0354 (3) | 1.10543 (11) | 0.0436 (5) | |
C7 | 0.0816 (3) | 0.9886 (2) | 1.04006 (10) | 0.0361 (4) | |
C8 | −0.0482 (3) | 0.8983 (2) | 0.99679 (10) | 0.0362 (4) | |
C9 | −0.0515 (3) | 0.8314 (3) | 0.87496 (10) | 0.0347 (4) | |
C10 | 0.0392 (3) | 0.7145 (3) | 0.84035 (11) | 0.0465 (5) | |
H10 | 0.1556 | 0.6800 | 0.8544 | 0.056* | |
C11 | −0.0441 (4) | 0.6494 (3) | 0.78494 (12) | 0.0581 (7) | |
H11 | 0.0171 | 0.5718 | 0.7610 | 0.070* | |
C12 | −0.2181 (4) | 0.6990 (3) | 0.76485 (12) | 0.0573 (7) | |
H12 | −0.2748 | 0.6536 | 0.7278 | 0.069* | |
C13 | −0.3084 (4) | 0.8156 (3) | 0.79935 (11) | 0.0504 (6) | |
H13 | −0.4260 | 0.8482 | 0.7857 | 0.061* | |
C14 | −0.2247 (3) | 0.8843 (3) | 0.85420 (10) | 0.0370 (5) | |
F1 | 0.53099 (17) | 1.15288 (17) | 0.99578 (7) | 0.0536 (4) | |
F2 | 0.5037 (2) | 1.23938 (19) | 1.12395 (8) | 0.0605 (4) | |
F3 | 0.1976 (3) | 1.17079 (19) | 1.19626 (7) | 0.0649 (4) | |
F4 | −0.0821 (2) | 1.0039 (2) | 1.14282 (7) | 0.0665 (5) | |
N1 | 0.0331 (2) | 0.9009 (2) | 0.93265 (8) | 0.0327 (4) | |
O3 | −0.3012 (2) | 1.0052 (2) | 0.88828 (9) | 0.0508 (4) | |
H3 | −0.4151 | 1.0014 | 0.8851 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0456 (9) | 0.0615 (10) | 0.0448 (8) | −0.0229 (9) | 0.0081 (8) | −0.0005 (8) |
C1 | 0.0269 (9) | 0.0343 (10) | 0.0357 (9) | 0.0038 (9) | −0.0016 (8) | 0.0047 (8) |
O1 | 0.0277 (7) | 0.0606 (9) | 0.0373 (7) | −0.0004 (8) | 0.0044 (6) | 0.0036 (7) |
C2 | 0.0316 (9) | 0.0315 (9) | 0.0363 (9) | 0.0013 (9) | 0.0001 (8) | 0.0026 (8) |
C3 | 0.0326 (10) | 0.0373 (11) | 0.0431 (11) | −0.0019 (9) | 0.0018 (9) | 0.0028 (9) |
C4 | 0.0407 (12) | 0.0434 (12) | 0.0459 (12) | −0.0069 (10) | −0.0082 (10) | −0.0049 (10) |
C5 | 0.0536 (14) | 0.0483 (12) | 0.0348 (10) | −0.0058 (12) | −0.0011 (10) | −0.0049 (10) |
C6 | 0.0447 (11) | 0.0485 (12) | 0.0375 (11) | −0.0113 (11) | 0.0070 (9) | −0.0007 (10) |
C7 | 0.0357 (10) | 0.0351 (10) | 0.0375 (10) | −0.0048 (9) | 0.0012 (8) | 0.0024 (9) |
C8 | 0.0356 (10) | 0.0365 (10) | 0.0364 (10) | −0.0050 (9) | 0.0026 (9) | 0.0027 (9) |
C9 | 0.0317 (10) | 0.0408 (10) | 0.0317 (9) | −0.0042 (9) | 0.0008 (8) | 0.0008 (8) |
C10 | 0.0433 (12) | 0.0507 (12) | 0.0454 (11) | 0.0071 (11) | 0.0029 (10) | −0.0024 (10) |
C11 | 0.0693 (17) | 0.0600 (15) | 0.0450 (13) | −0.0025 (14) | 0.0124 (12) | −0.0147 (12) |
C12 | 0.0640 (16) | 0.0733 (17) | 0.0347 (10) | −0.0183 (15) | −0.0031 (12) | −0.0105 (12) |
C13 | 0.0398 (12) | 0.0715 (15) | 0.0400 (11) | −0.0061 (13) | −0.0083 (11) | 0.0012 (12) |
C14 | 0.0302 (10) | 0.0450 (11) | 0.0357 (10) | −0.0034 (9) | 0.0029 (8) | 0.0006 (9) |
F1 | 0.0371 (7) | 0.0655 (9) | 0.0582 (8) | −0.0169 (7) | 0.0095 (6) | −0.0085 (7) |
F2 | 0.0520 (8) | 0.0712 (9) | 0.0582 (8) | −0.0209 (8) | −0.0087 (7) | −0.0143 (8) |
F3 | 0.0724 (10) | 0.0821 (10) | 0.0402 (7) | −0.0192 (10) | 0.0055 (8) | −0.0178 (7) |
F4 | 0.0600 (9) | 0.0929 (12) | 0.0465 (7) | −0.0322 (9) | 0.0211 (7) | −0.0149 (8) |
N1 | 0.0252 (8) | 0.0406 (9) | 0.0322 (8) | 0.0001 (7) | −0.0006 (6) | −0.0006 (7) |
O3 | 0.0272 (7) | 0.0599 (10) | 0.0653 (10) | 0.0069 (8) | −0.0039 (8) | −0.0126 (9) |
O2—C8 | 1.200 (3) | C8—N1 | 1.409 (3) |
C1—O1 | 1.206 (2) | C9—C10 | 1.382 (3) |
C1—N1 | 1.391 (3) | C9—C14 | 1.386 (3) |
C1—C2 | 1.492 (3) | C9—N1 | 1.434 (3) |
C2—C3 | 1.364 (3) | C10—C11 | 1.377 (3) |
C2—C7 | 1.387 (3) | C10—H10 | 0.9300 |
C3—F1 | 1.332 (2) | C11—C12 | 1.379 (4) |
C3—C4 | 1.389 (3) | C11—H11 | 0.9300 |
C4—F2 | 1.332 (2) | C12—C13 | 1.377 (4) |
C4—C5 | 1.371 (3) | C12—H12 | 0.9300 |
C5—F3 | 1.332 (3) | C13—C14 | 1.382 (3) |
C5—C6 | 1.385 (3) | C13—H13 | 0.9300 |
C6—F4 | 1.333 (3) | C14—O3 | 1.358 (3) |
C6—C7 | 1.371 (3) | O3—H3 | 0.8200 |
C7—C8 | 1.489 (3) | ||
O1—C1—N1 | 125.62 (19) | N1—C8—C7 | 105.14 (16) |
O1—C1—C2 | 128.77 (18) | C10—C9—C14 | 120.6 (2) |
N1—C1—C2 | 105.60 (16) | C10—C9—N1 | 120.38 (19) |
C3—C2—C7 | 120.82 (19) | C14—C9—N1 | 118.98 (19) |
C3—C2—C1 | 130.82 (19) | C11—C10—C9 | 119.6 (2) |
C7—C2—C1 | 108.30 (17) | C11—C10—H10 | 120.2 |
F1—C3—C2 | 123.0 (2) | C9—C10—H10 | 120.2 |
F1—C3—C4 | 118.1 (2) | C10—C11—C12 | 120.1 (3) |
C2—C3—C4 | 118.8 (2) | C10—C11—H11 | 120.0 |
F2—C4—C5 | 119.9 (2) | C12—C11—H11 | 120.0 |
F2—C4—C3 | 119.6 (2) | C13—C12—C11 | 120.3 (2) |
C5—C4—C3 | 120.5 (2) | C13—C12—H12 | 119.9 |
F3—C5—C4 | 119.6 (2) | C11—C12—H12 | 119.9 |
F3—C5—C6 | 119.8 (2) | C12—C13—C14 | 120.2 (2) |
C4—C5—C6 | 120.5 (2) | C12—C13—H13 | 119.9 |
F4—C6—C7 | 122.4 (2) | C14—C13—H13 | 119.9 |
F4—C6—C5 | 118.7 (2) | O3—C14—C13 | 123.3 (2) |
C7—C6—C5 | 118.9 (2) | O3—C14—C9 | 117.53 (19) |
C6—C7—C2 | 120.4 (2) | C13—C14—C9 | 119.2 (2) |
C6—C7—C8 | 131.2 (2) | C1—N1—C8 | 112.31 (16) |
C2—C7—C8 | 108.38 (18) | C1—N1—C9 | 124.25 (16) |
O2—C8—N1 | 125.6 (2) | C8—N1—C9 | 123.37 (17) |
O2—C8—C7 | 129.3 (2) | C14—O3—H3 | 109.5 |
O1—C1—C2—C3 | 1.8 (4) | C6—C7—C8—O2 | −6.8 (4) |
N1—C1—C2—C3 | −176.8 (2) | C2—C7—C8—O2 | 174.6 (2) |
O1—C1—C2—C7 | 179.0 (2) | C6—C7—C8—N1 | 173.8 (2) |
N1—C1—C2—C7 | 0.4 (2) | C2—C7—C8—N1 | −4.8 (2) |
C7—C2—C3—F1 | −179.78 (19) | C14—C9—C10—C11 | −0.4 (3) |
C1—C2—C3—F1 | −3.0 (4) | N1—C9—C10—C11 | −179.8 (2) |
C7—C2—C3—C4 | −0.9 (3) | C9—C10—C11—C12 | −1.0 (4) |
C1—C2—C3—C4 | 175.9 (2) | C10—C11—C12—C13 | 1.1 (4) |
F1—C3—C4—F2 | −1.1 (3) | C11—C12—C13—C14 | 0.3 (4) |
C2—C3—C4—F2 | 180.0 (2) | C12—C13—C14—O3 | 176.4 (2) |
F1—C3—C4—C5 | 178.5 (2) | C12—C13—C14—C9 | −1.7 (3) |
C2—C3—C4—C5 | −0.5 (3) | C10—C9—C14—O3 | −176.4 (2) |
F2—C4—C5—F3 | 1.3 (4) | N1—C9—C14—O3 | 3.0 (3) |
C3—C4—C5—F3 | −178.3 (2) | C10—C9—C14—C13 | 1.7 (3) |
F2—C4—C5—C6 | −179.0 (2) | N1—C9—C14—C13 | −178.8 (2) |
C3—C4—C5—C6 | 1.4 (4) | O1—C1—N1—C8 | 177.7 (2) |
F3—C5—C6—F4 | 0.3 (4) | C2—C1—N1—C8 | −3.6 (2) |
C4—C5—C6—F4 | −179.3 (2) | O1—C1—N1—C9 | 0.6 (3) |
F3—C5—C6—C7 | 178.8 (2) | C2—C1—N1—C9 | 179.30 (18) |
C4—C5—C6—C7 | −0.9 (4) | O2—C8—N1—C1 | −174.2 (2) |
F4—C6—C7—C2 | 177.9 (2) | C7—C8—N1—C1 | 5.2 (2) |
C5—C6—C7—C2 | −0.5 (3) | O2—C8—N1—C9 | 2.9 (3) |
F4—C6—C7—C8 | −0.6 (4) | C7—C8—N1—C9 | −177.65 (18) |
C5—C6—C7—C8 | −179.0 (2) | C10—C9—N1—C1 | 56.7 (3) |
C3—C2—C7—C6 | 1.4 (3) | C14—C9—N1—C1 | −122.8 (2) |
C1—C2—C7—C6 | −176.1 (2) | C10—C9—N1—C8 | −120.0 (2) |
C3—C2—C7—C8 | −179.76 (19) | C14—C9—N1—C8 | 60.5 (3) |
C1—C2—C7—C8 | 2.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1i | 0.82 | 1.99 | 2.804 (2) | 175 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C14H5F4NO3 |
Mr | 311.19 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 7.1741 (14), 8.5862 (17), 19.994 (4) |
V (Å3) | 1231.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.36 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.945, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9661, 1421, 1357 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.078, 1.09 |
No. of reflections | 1421 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Bruker, 2002).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1i | 0.82 | 1.99 | 2.804 (2) | 175.3 |
Symmetry code: (i) x−1, y, z. |
N-Substituted 2,3,4,5-tetrafluorophthalimides are an important class of compounds because of their interesting biological activities (Collin et al., 2001; Miyachi et al., 1997; Niwayama et al., 1996). They are intermediates for the synthesis of fluoroquinolone antibiotics (Cai et al., 2006).
The bond lengths and angles of the title compound are within normal ranges (Allen et al., 1987). The isoindole unit (atoms N1/C1—C8) is essentially planar, with maximum deviation of 0.0493 (21) Å for atom C8. The dihedral angle between the isoindole unit and the hydroxyphenyl ring is 56.88 (6)°, which is less than that found in 2-(2-hydroxyphenyl)isoindoline-1,3-dione [71.8 (2)°] (Li et al., 2007) and 4,5,6,7-tetrachloro-2-(2-hydroxyphenyl)isoindoline-1,3-dione [63.78 (5)°] (Fun et al., 2007). The crystal structure is stabilized by an intermolecular O—H···O hydrogen bond (Table 1).