4,5,6,7-Tetra­fluoro-2-(2-hydroxy­phen­yl)isoindoline-1,3-dione

The crystal structure of the title compound, C₁₄H₅F₄NO₃, which was synthesized by the condensation of tetra­fluoro­phthalic anhydride with 2-amino­phenol, is stabilized by an inter­molecular O—H...O hydrogen bond. The dihedral angle between the phthalimide and hydroxy­phenyl planes is 56.88 (6)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

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S1. Comment

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).

Related literature

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).

S2. Experimental

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).

S3. Refinement

H atoms were placed at calculated positions and refined in the riding-model approximation, with C—H = 0.93 Å and U_iso(H) = 1.2Ueq(C) for aromatic H atoms, O—H = 0.82 Å and U_iso(H) = 1.5Ueq(O) for the hydroxyl H atom. In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Computing details

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).

Figures

Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30% probability level.

4,5,6,7-Tetrafluoro-2-(2-hydroxyphenyl)isoindoline-1,3-dione

Crystal data

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) Å^3	Block, pale yellow
Z = 4	0.36 × 0.20 × 0.16 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 0.1954P] where P = (Fo^2 + 2Fc^2)/3
1421 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.82	1.99	2.804 (2)	175

Symmetry code: (i) x−1, y, z.