N (2 Fluorophenyl)phthalimide

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organic papers

o408

Xuet al. _C

14H8FNO2 doi:10.1107/S1600536805041206 Acta Cryst.(2006). E62, o408–o409

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

N

-(2-Fluorophenyl)phthalimide

Dan Xu,aYu-Quan Shi,a* Bin Chen,aYu-Hong Chengband Xu Gaoc

a_{Department of Chemistry, College of Sciences,}

Tianjin University, Tianjin 300072, People’s Republic of China,b_{Department of Petroleum}

and Chemical Engineering, Tianjin Engineering Technical Institute, Tianjin, 300280, People’s Republic of China, andcDepartment of Chemistry, Anshan Normal University, Liaoning Province 114005, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 294 K

Mean(C–C) = 0.003 A˚ Disorder in main residue

Rfactor = 0.037

wRfactor = 0.104

Data-to-parameter ratio = 12.9

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

In the title compound, C14H8FNO2, the dihedral angle

between the two planar ring systems is 59.95 (4)_.

Comment

The crystal structure of the title compound, (I), has been determined in order to elucidate the molecular conformation. The dihedral angle between the benzene ring and the phthalimide plane is 59.95 (4)_.

Experimental

Compound (I) was prepared from phthalic anhydride and 2-fluoro-aniline (Barchin et al., 2002). An acetic acid solution of phthalic anhydride (14.8 g, 100 mmol) and 2-fluoroaniline (11.1 g, 100 mmol) was refluxed overnight, and then filtered. The crude product was washed with water three times, and dried. The compound (I) was recrystallized from ethyl acetate (m.p. 465 K).

Crystal data

C14H8FNO2

Mr= 241.21 Orthorhombic,Pbca a= 11.622 (3) A˚

b= 7.8368 (16) A˚

c= 24.017 (5) A˚

V= 2187.5 (8) A˚3

Z= 8

Dx= 1.465 Mg m

3

MoKradiation Cell parameters from 1794

reflections

= 2.4–22.5

= 0.11 mm1

T= 294 (2) K Prism, white

0.260.200.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin= 0.967,Tmax= 0.983 11486 measured reflections

2240 independent reflections 1169 reflections withI> 2(I)

Rint= 0.066

max= 26.4

h=13!14

k=7!9

l=29!29

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Refinement

Refinement onF2 R[F2_{> 2}₍_F2_{)] = 0.037}

wR(F2) = 0.104

S= 0.99 2240 reflections 174 parameters

H-atom parameters constrained

w= 1/[2

(Fo2) + (0.0411P)2 + 0.2748P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001

max= 0.13 e A˚

3 min=0.12 e A˚

3

Extinction correction:SHELXTL

Extinction coefficient: 0.0218 (14)

Table 1

Selected geometric parameters (A˚ ,_).

F1—C2 1.307 (2) F10

—C6 1.344 (4) N1—C1 1.426 (2) C1—C2 1.374 (3)

C4—C5 1.372 (3) C7—C8 1.475 (3) C8—C13 1.382 (3) C13—C14 1.489 (3)

C2—C1—N1 120.85 (18) F1—C2—C1 118.73 (19) C1—C2—C3 122.5 (2) F10_—C6—C1 _{114.4 (2)}

C10—C11—C12 120.9 (2) O2—C14—N1 125.17 (18) O2—C14—C13 129.19 (19) N1—C14—C13 105.64 (16)

The F atom is disordered over two ortho positions with refined occupancies of 0.681 (3) and 0.319 (3). All H atoms were initially located in a difference Fourier map. All H atoms were then constrained to an ideal geometry, with C—H distances of 0.93 A˚ and

Uiso(H) = 1.2Ueq(C).

Data collection:SMART(Bruker, 1997); cell refinement:SAINT

(Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

SHELXTL (Bruker, 1997); software used to prepare material for publication:SHELXTL.

We are indebted to the National Natural Science Founda-tion, People’s Republic of China (grant No. 60071027) and the Natural Science Foudation of Tianjin City, People’s Republic of China (grant No. 023603811) for financial support.

References

Barchin, B. M., Cuadro, A. M. & Alvarez-Builla, J. (2002).Synlett,2, 343–345. Bruker (1997).SMART,SAINTandSHELXTL(Version 5.10). Bruker AXS

Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.

Sheldrick, G. M. (2002).SADABS. Version 2.03. University of Go¨ttingen, Germany.

Figure 2

[image:2.610.314.563.72.186.2]

The crystal packing of (I), viewed along thebaxis. Figure 1

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supporting information

sup-1 Acta Cryst. (2006). E62, o408–o409

supporting information

Acta Cryst. (2006). E62, o408–o409 [https://doi.org/10.1107/S1600536805041206]

N

-(2-Fluorophenyl)phthalimide

Dan Xu, Yu-Quan Shi, Bin Chen, Yu-Hong Cheng and Xu Gao

N-(2-Fluorophenyl)phthalimide

Crystal data

C14H8FNO2

Mr = 241.21

Orthorhombic, Pbca

Hall symbol: -P 2ac 2ab

a = 11.622 (3) Å

b = 7.8368 (16) Å

c = 24.017 (5) Å

V = 2187.5 (8) Å3

Z = 8

F(000) = 992

Dx = 1.465 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1794 reflections

θ = 2.4–22.5°

µ = 0.11 mm−1

T = 294 K Prism, white

0.26 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin = 0.967, Tmax = 0.983

11486 measured reflections 2240 independent reflections 1169 reflections with I > 2σ(I)

Rint = 0.066

θmax = 26.4°, θmin = 1.7°

h = −13→14

k = −7→9

l = −29→29

Refinement

Refinement on F2

Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.037}

wR(F2_{) = 0.104}

S = 0.99 2240 reflections 174 parameters 2 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2₍_F

o2) + (0.0411P)2 + 0.2748P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

Extinction correction: SHELXTL, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2_θ_)]-1/4

Extinction coefficient: 0.0218 (14)

Special details

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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_{> 2}_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₎

x y z Uiso*/Ueq Occ. (<1)

F1 0.45336 (15) −0.0205 (2) 0.31890 (7) 0.0741 (7) 0.681 (3) F1′ 0.8064 (3) 0.2372 (5) 0.32862 (16) 0.0722 (16) 0.319 (3) N1 0.61566 (13) 0.14038 (19) 0.38251 (6) 0.0461 (4)

O1 0.78204 (14) −0.0051 (2) 0.40639 (6) 0.0779 (5) O2 0.45026 (12) 0.30430 (19) 0.38866 (6) 0.0658 (5) C1 0.62486 (17) 0.1271 (2) 0.32346 (8) 0.0459 (5) C2 0.54049 (18) 0.0479 (3) 0.29278 (9) 0.0540 (6)

H2 0.4761 0.0054 0.3111 0.065* 0.319 (3) C3 0.5477 (2) 0.0293 (3) 0.23594 (9) 0.0636 (6)

H3 0.4889 −0.0235 0.2160 0.076* C4 0.6433 (2) 0.0902 (3) 0.20940 (9) 0.0660 (7) H4 0.6501 0.0774 0.1710 0.079* C5 0.7294 (2) 0.1700 (3) 0.23856 (9) 0.0664 (6) H5 0.7940 0.2115 0.2201 0.080* C6 0.71918 (19) 0.1882 (3) 0.29553 (9) 0.0591 (6)

H6 0.7773 0.2428 0.3153 0.071* 0.681 (3) C7 0.69670 (18) 0.0731 (3) 0.41974 (8) 0.0498 (5)

C8 0.65634 (16) 0.1192 (2) 0.47600 (8) 0.0443 (5) C9 0.70264 (18) 0.0835 (3) 0.52747 (9) 0.0553 (6) H9 0.7694 0.0190 0.5309 0.066* C10 0.6470 (2) 0.1463 (3) 0.57373 (9) 0.0620 (6) H10 0.6773 0.1253 0.6089 0.074* C11 0.54689 (19) 0.2401 (3) 0.56882 (9) 0.0614 (6) H11 0.5105 0.2802 0.6007 0.074* C12 0.49990 (17) 0.2751 (3) 0.51708 (9) 0.0562 (6) H12 0.4325 0.3381 0.5136 0.067* C13 0.55637 (15) 0.2134 (2) 0.47096 (8) 0.0441 (5) C14 0.52877 (17) 0.2300 (2) 0.41065 (8) 0.0477 (5)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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supporting information

sup-3 Acta Cryst. (2006). E62, o408–o409

C4 0.0840 (19) 0.0636 (16) 0.0505 (13) 0.0090 (13) −0.0001 (13) −0.0001 (12) C5 0.0707 (16) 0.0647 (15) 0.0637 (16) 0.0013 (12) 0.0156 (13) −0.0058 (12) C6 0.0537 (14) 0.0629 (15) 0.0607 (15) −0.0021 (12) −0.0038 (12) −0.0126 (11) C7 0.0498 (13) 0.0439 (12) 0.0557 (13) 0.0051 (10) −0.0090 (10) −0.0036 (10) C8 0.0437 (11) 0.0433 (11) 0.0459 (12) −0.0027 (9) −0.0059 (10) 0.0033 (10) C9 0.0496 (13) 0.0583 (14) 0.0578 (14) −0.0016 (10) −0.0106 (11) 0.0072 (11) C10 0.0606 (15) 0.0762 (16) 0.0492 (13) −0.0112 (13) −0.0063 (11) 0.0086 (12) C11 0.0619 (15) 0.0749 (16) 0.0473 (14) −0.0083 (13) 0.0065 (11) 0.0029 (11) C12 0.0472 (12) 0.0642 (14) 0.0573 (14) 0.0023 (10) 0.0029 (11) 0.0076 (11) C13 0.0426 (11) 0.0430 (11) 0.0468 (12) −0.0054 (9) −0.0029 (9) 0.0058 (9) C14 0.0415 (12) 0.0467 (12) 0.0548 (13) −0.0009 (10) −0.0038 (10) 0.0062 (10)

Geometric parameters (Å, º)

F1—C2 1.307 (2) C5—C6 1.381 (3) F1′—C6 1.344 (4) C5—H5 0.9300 N1—C7 1.402 (2) C6—H6 0.9300 N1—C14 1.403 (2) C7—C8 1.475 (3) N1—C1 1.426 (2) C8—C9 1.377 (2) O1—C7 1.209 (2) C8—C13 1.382 (3) O2—C14 1.204 (2) C9—C10 1.377 (3) C1—C6 1.371 (3) C9—H9 0.9300 C1—C2 1.374 (3) C10—C11 1.381 (3) C2—C3 1.376 (3) C10—H10 0.9300 C2—H2 0.9300 C11—C12 1.385 (3) C3—C4 1.367 (3) C11—H11 0.9300 C3—H3 0.9300 C12—C13 1.375 (3) C4—C5 1.372 (3) C12—H12 0.9300 C4—H4 0.9300 C13—C14 1.489 (3)

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C4—C5—H5 120.3 C12—C13—C8 121.23 (18) C6—C5—H5 120.3 C12—C13—C14 130.53 (18) F1′—C6—C1 114.4 (2) C8—C13—C14 108.25 (17) F1′—C6—C5 123.4 (3) O2—C14—N1 125.17 (18) C1—C6—C5 121.2 (2) O2—C14—C13 129.19 (19) C1—C6—H6 119.4 N1—C14—C13 105.64 (16) C5—C6—H6 119.4

N (2 Fluoro­phen­yl)phthalimide

organic papers

o408

N

-(2-Fluorophenyl)phthalimide

supporting information

supporting information

N

-(2-Fluorophenyl)phthalimide

Dan Xu, Yu-Quan Shi, Bin Chen, Yu-Hong Cheng and Xu Gao

supporting information

N (2 Fluorophenyl)phthalimide