Tetra­fluoro-N-phenyl­phthalimide

Wen, F.; Ni, R.-J.; Yao, C.

doi:10.1107/S1600536807027286

Tetrafluoro-N-phenylphthalimide

In the molecule of the title compound, C₁₄H₅F₄NO₂, the dihedral angles between the planar rings A (phenyl), B (five-membered) and C (fused benzene) are A/B = 50.13 (3)°, A/C = 48.34 (3)° and B/C = 3.80 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027286/hk2269sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027286/hk2269Isup2.hkl Contains datablock I

CCDC reference: 654912

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.035
wR factor = 0.090
Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.31
PLAT431_ALERT_2_C Short Inter HL..A Contact  F3     ..  O1      ..       2.97 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C7      ..       2.96 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           25.99
           From the CIF: _reflns_number_total               1388
           Count of symmetry unique reflns         1391
           Completeness (_total/calc)             99.78%
           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
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   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

Comment top

The title compound, (I), can be utilized to synthsize 2,3,4,5-tetrafluoro- benzoic acid, it is an important intermediate of fluoroquinolone antibiotics (Cai et al., 2006). We report herein the crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angles between the planar rings A (C1—C6), B (N/C7—C10) and C (C9—C14) are A/B = 50.13 (3)°, A/C = 48.34 (3)° and B/C = 3.80 (2)°.

Related literature top

For general backgroud, see: Cai et al. (2006); Allen et al. (1987). For related literature, see: Nowak & Lin (1991).

Experimental top

The title compound, (I), was prepared by adding tetrachloro-N-phenylphthalimide (100 g, 0.28 mol) to 413 g sulfolane solution of KF (193 g, 3.3 mol) at 433 K (Nowak & Lin, 1991). After stirring for 3 h, the mixture was filtered hot, the product was separated from the sulfolane by the addition of cold water (1900 ml). The yellow solid, was recrystallized by the addition of acetic acid. Then, the crystals of compound (I) were obtained by evaporating the solvent ethyl acetate slowly at room temperature for about 7 d.

Structure description top

For general backgroud, see: Cai et al. (2006); Allen et al. (1987). For related literature, see: Nowak & Lin (1991).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Tetrafluoro-N-phenylphthalimide top

Crystal data top

C₁₄H₅F₄NO₂	F(000) = 592
M_r = 295.19	D_x = 1.638 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.0960 (14) Å	θ = 10–13°
b = 8.4060 (17) Å	µ = 0.15 mm⁻¹
c = 20.068 (4) Å	T = 298 K
V = 1197.0 (4) Å³	Block, colorless
Z = 4	0.30 × 0.30 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1079 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 26.0°, θ_min = 2.0°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
T_min = 0.955, T_max = 0.985	l = 0→24
2348 measured reflections	3 standard reflections every 120 min
1388 independent reflections	intensity decay: none

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
1388 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₄H₅F₄NO₂	V = 1197.0 (4) Å³
M_r = 295.19	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.0960 (14) Å	µ = 0.15 mm⁻¹
b = 8.4060 (17) Å	T = 298 K
c = 20.068 (4) Å	0.30 × 0.30 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1079 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.955, T_max = 0.985	3 standard reflections every 120 min
2348 measured reflections	intensity decay: none
1388 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
1388 reflections	Δρ_min = −0.16 e Å⁻³
190 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 > 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 (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.7900 (3)	1.1852 (2)	−0.18876 (8)	0.0824 (6)
F2	0.4777 (3)	1.2338 (2)	−0.11603 (10)	0.0814 (7)
F3	0.4567 (2)	1.1333 (2)	0.01142 (9)	0.0673 (5)
F4	1.0865 (3)	1.0230 (2)	−0.13876 (8)	0.0734 (6)
O1	1.2119 (3)	0.8510 (2)	−0.01010 (9)	0.0576 (5)
O2	0.6970 (3)	0.9697 (3)	0.11857 (9)	0.0606 (5)
N	0.9795 (3)	0.8960 (3)	0.06903 (10)	0.0454 (5)
C1	1.0590 (6)	0.6500 (4)	0.21979 (15)	0.0730 (10)
H1A	0.9942	0.5770	0.2460	0.088*
C2	0.9740 (5)	0.7132 (4)	0.16367 (15)	0.0605 (8)
H2A	0.8535	0.6809	0.1514	0.073*
C3	1.0692 (4)	0.8240 (3)	0.12618 (12)	0.0470 (6)
C4	1.2493 (4)	0.8701 (4)	0.14324 (14)	0.0566 (8)
H4A	1.3134	0.9445	0.1175	0.068*
C5	1.3328 (5)	0.8057 (4)	0.19844 (14)	0.0682 (9)
H5A	1.4542	0.8366	0.2102	0.082*
C6	1.2381 (6)	0.6949 (5)	0.23682 (15)	0.0754 (10)
H6A	1.2959	0.6509	0.2741	0.090*
C7	0.7977 (4)	0.9623 (3)	0.07029 (13)	0.0478 (6)
C8	1.0603 (4)	0.9040 (3)	0.00558 (13)	0.0461 (6)
C9	0.9221 (4)	0.9915 (3)	−0.03620 (13)	0.0450 (6)
C10	0.7641 (4)	1.0220 (3)	0.00212 (12)	0.0457 (6)
C11	0.6128 (4)	1.1016 (3)	−0.02440 (15)	0.0511 (7)
C12	0.6241 (4)	1.1549 (3)	−0.08918 (15)	0.0574 (8)
C13	0.7831 (5)	1.1282 (4)	−0.12682 (14)	0.0582 (8)
C14	0.9322 (4)	1.0455 (3)	−0.10040 (14)	0.0536 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0990 (15)	0.0909 (13)	0.0573 (10)	0.0218 (13)	−0.0001 (11)	0.0167 (10)
F2	0.0773 (14)	0.0777 (12)	0.0893 (14)	0.0330 (12)	−0.0168 (11)	0.0018 (11)
F3	0.0498 (9)	0.0643 (11)	0.0878 (12)	0.0148 (9)	0.0115 (9)	−0.0076 (9)
F4	0.0708 (11)	0.0915 (13)	0.0578 (9)	0.0197 (12)	0.0179 (9)	0.0110 (9)
O1	0.0524 (11)	0.0644 (12)	0.0560 (11)	0.0151 (11)	0.0074 (10)	−0.0006 (10)
O2	0.0502 (11)	0.0740 (14)	0.0576 (11)	−0.0024 (12)	0.0118 (10)	−0.0086 (10)
N	0.0443 (12)	0.0505 (12)	0.0413 (10)	−0.0034 (11)	0.0016 (10)	−0.0022 (10)
C1	0.088 (3)	0.075 (2)	0.0565 (18)	−0.005 (2)	0.0140 (17)	0.0132 (16)
C2	0.0644 (19)	0.0591 (17)	0.0579 (16)	−0.0104 (17)	0.0043 (16)	0.0007 (15)
C3	0.0492 (15)	0.0501 (15)	0.0415 (13)	−0.0017 (14)	0.0028 (12)	−0.0029 (12)
C4	0.0528 (17)	0.068 (2)	0.0487 (15)	−0.0076 (16)	0.0000 (13)	0.0009 (14)
C5	0.0546 (18)	0.097 (2)	0.0527 (16)	−0.0034 (19)	−0.0084 (15)	0.0002 (18)
C6	0.083 (2)	0.095 (3)	0.0487 (16)	0.013 (2)	0.0006 (17)	0.0082 (18)
C7	0.0450 (14)	0.0479 (15)	0.0507 (14)	−0.0069 (14)	0.0029 (13)	−0.0112 (12)
C8	0.0462 (14)	0.0445 (14)	0.0477 (14)	0.0008 (13)	0.0036 (13)	−0.0069 (12)
C9	0.0450 (14)	0.0401 (13)	0.0498 (14)	0.0021 (12)	0.0018 (12)	−0.0047 (11)
C10	0.0468 (14)	0.0376 (13)	0.0525 (14)	−0.0007 (12)	0.0042 (12)	−0.0081 (12)
C11	0.0446 (14)	0.0431 (14)	0.0656 (17)	0.0031 (14)	0.0037 (14)	−0.0120 (13)
C12	0.0617 (18)	0.0432 (16)	0.0672 (18)	0.0119 (15)	−0.0094 (15)	−0.0059 (14)
C13	0.070 (2)	0.0550 (17)	0.0494 (14)	0.0080 (17)	0.0001 (15)	−0.0001 (14)
C14	0.0577 (17)	0.0534 (16)	0.0497 (14)	0.0091 (15)	0.0065 (14)	−0.0033 (13)

Geometric parameters (Å, º) top

F1—C13	1.333 (3)	C3—C4	1.379 (4)
F2—C12	1.345 (3)	C4—C5	1.368 (4)
F3—C11	1.347 (3)	C4—H4A	0.9300
F4—C14	1.352 (3)	C5—C6	1.383 (5)
O1—C8	1.206 (3)	C5—H5A	0.9300
O2—C7	1.206 (3)	C6—H6A	0.9300
N—C8	1.398 (3)	C7—C10	1.477 (4)
N—C7	1.405 (4)	C8—C9	1.485 (4)
N—C3	1.445 (3)	C9—C14	1.368 (4)
C1—C6	1.369 (5)	C9—C10	1.384 (3)
C1—C2	1.383 (5)	C10—C11	1.373 (4)
C1—H1A	0.9300	C11—C12	1.377 (4)
C2—C3	1.375 (4)	C12—C13	1.376 (4)
C2—H2A	0.9300	C13—C14	1.373 (4)

C8—N—C7	112.0 (2)	N—C7—C10	105.5 (2)
C8—N—C3	124.2 (2)	O1—C8—N	125.9 (3)
C7—N—C3	123.8 (2)	O1—C8—C9	128.6 (3)
C6—C1—C2	120.1 (3)	N—C8—C9	105.5 (2)
C6—C1—H1A	119.9	C14—C9—C10	120.3 (3)
C2—C1—H1A	119.9	C14—C9—C8	131.4 (3)
C3—C2—C1	119.4 (3)	C10—C9—C8	108.2 (2)
C3—C2—H2A	120.3	C11—C10—C9	120.6 (2)
C1—C2—H2A	120.3	C11—C10—C7	130.6 (2)
C2—C3—C4	120.7 (3)	C9—C10—C7	108.7 (2)
C2—C3—N	120.1 (3)	F3—C11—C10	122.2 (3)
C4—C3—N	119.2 (3)	F3—C11—C12	119.2 (3)
C5—C4—C3	119.4 (3)	C10—C11—C12	118.6 (3)
C5—C4—H4A	120.3	F2—C12—C13	119.6 (3)
C3—C4—H4A	120.3	F2—C12—C11	119.6 (3)
C4—C5—C6	120.5 (3)	C13—C12—C11	120.9 (3)
C4—C5—H5A	119.8	F1—C13—C14	120.9 (3)
C6—C5—H5A	119.8	F1—C13—C12	118.9 (3)
C1—C6—C5	119.9 (3)	C14—C13—C12	120.2 (3)
C1—C6—H6A	120.1	F4—C14—C9	122.2 (3)
C5—C6—H6A	120.1	F4—C14—C13	118.4 (2)
O2—C7—N	125.4 (3)	C9—C14—C13	119.4 (3)
O2—C7—C10	129.1 (3)

C6—C1—C2—C3	−1.6 (5)	C14—C9—C10—C7	−175.3 (2)
C1—C2—C3—C4	1.3 (4)	C8—C9—C10—C7	2.5 (3)
C1—C2—C3—N	−177.4 (3)	O2—C7—C10—C11	0.5 (5)
C8—N—C3—C2	−129.0 (3)	N—C7—C10—C11	−177.8 (3)
C7—N—C3—C2	49.0 (4)	O2—C7—C10—C9	177.9 (3)
C8—N—C3—C4	52.3 (4)	N—C7—C10—C9	−0.4 (3)
C7—N—C3—C4	−129.7 (3)	C9—C10—C11—F3	180.0 (2)
C2—C3—C4—C5	−0.6 (4)	C7—C10—C11—F3	−2.9 (5)
N—C3—C4—C5	178.1 (3)	C9—C10—C11—C12	−2.1 (4)
C3—C4—C5—C6	0.2 (5)	C7—C10—C11—C12	175.1 (3)
C2—C1—C6—C5	1.2 (6)	F3—C11—C12—F2	−1.7 (4)
C4—C5—C6—C1	−0.5 (5)	C10—C11—C12—F2	−179.7 (3)
C8—N—C7—O2	179.6 (3)	F3—C11—C12—C13	178.4 (3)
C3—N—C7—O2	1.4 (4)	C10—C11—C12—C13	0.4 (4)
C8—N—C7—C10	−2.1 (3)	F2—C12—C13—F1	1.8 (4)
C3—N—C7—C10	179.7 (2)	C11—C12—C13—F1	−178.4 (3)
C7—N—C8—O1	−177.2 (3)	F2—C12—C13—C14	−178.9 (3)
C3—N—C8—O1	1.0 (5)	C11—C12—C13—C14	1.0 (5)
C7—N—C8—C9	3.5 (3)	C10—C9—C14—F4	177.7 (3)
C3—N—C8—C9	−178.3 (2)	C8—C9—C14—F4	0.5 (5)
O1—C8—C9—C14	−5.5 (5)	C10—C9—C14—C13	−1.0 (4)
N—C8—C9—C14	173.8 (3)	C8—C9—C14—C13	−178.2 (3)
O1—C8—C9—C10	177.0 (3)	F1—C13—C14—F4	−0.1 (5)
N—C8—C9—C10	−3.7 (3)	C12—C13—C14—F4	−179.4 (3)
C14—C9—C10—C11	2.4 (4)	F1—C13—C14—C9	178.6 (3)
C8—C9—C10—C11	−179.8 (2)	C12—C13—C14—C9	−0.7 (5)

Experimental details

Crystal data
Chemical formula	C₁₄H₅F₄NO₂
M_r	295.19
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.0960 (14), 8.4060 (17), 20.068 (4)
V (Å³)	1197.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.955, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	2348, 1388, 1079
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 1.03
No. of reflections	1388
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top

F1—C13	1.333 (3)	O2—C7	1.206 (3)
F2—C12	1.345 (3)	N—C8	1.398 (3)
F3—C11	1.347 (3)	N—C7	1.405 (4)
F4—C14	1.352 (3)	N—C3	1.445 (3)
O1—C8	1.206 (3)

C8—N—C7	112.0 (2)	N—C8—C9	105.5 (2)
C8—N—C3	124.2 (2)	F3—C11—C10	122.2 (3)
C7—N—C3	123.8 (2)	F3—C11—C12	119.2 (3)
C2—C3—N	120.1 (3)	F2—C12—C13	119.6 (3)
C4—C3—N	119.2 (3)	F2—C12—C11	119.6 (3)
O2—C7—N	125.4 (3)	F1—C13—C14	120.9 (3)
O2—C7—C10	129.1 (3)	F1—C13—C12	118.9 (3)
N—C7—C10	105.5 (2)	F4—C14—C9	122.2 (3)
O1—C8—N	125.9 (3)	F4—C14—C13	118.4 (2)
O1—C8—C9	128.6 (3)

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Tetra­fluoro-N-phenyl­phthalimide

Supporting information

Key indicators

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Tetrafluoro-N-phenylphthalimide