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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2432
https://doi.org/10.1107/S1600536810032575

4,5,6,7-Tetra­chloro-N-(2-fluoro­phen­yl)phthalimide

Xian-Shu Fu,a Xiao-Ping Yu,a Wei-Min Wanga* and Fang Lina

aCollege of Life Sciences, China Jiliang University, Hangzhou 310018, People's Republic of China
*Correspondence e-mail: clshangzhou@yahoo.com.cn

(Received 17 June 2010; accepted 13 August 2010; online 28 August 2010)

In the title compound, C14H4Cl4FNO2, the benzene ring and the phthalimide plane are nearly planar, the maximum deviations being 0.005 (2) and 0.010 (2) Å, respectively, but the mol­ecule as a whole is not planar: the dihedral angle between the two planar ring systems is 68.06 (10)°. A short Cl⋯O contact of 2.914 (2) Å exists in the crystal structure.

Related literature

The title compound is an inter­mediate in the synthesis of organic electroluminescent materials; see: Han & Kay (2005[Han, K. J. & Kay, K. Y. (2005). J. Korean Chem. Soc. 49, 233-238.]). For details of the synthesis, see: Valkonen et al. (2007[Valkonen, A., Lahtinen, T. & Rissanen, K. (2007). Acta Cryst. E63, o472-o473.]); Barchin et al. (2002[Barchin, B. M., Cuadro, A. M. & Alvarez-Builla, J. (2002). Synlett, 2, 343-345.]). For related structures, see: Xu et al. (2006[Xu, D., Shi, Y.-Q., Chen, B., Cheng, Y.-H. & Gao, X. (2006). Acta Cryst. E62, o408-o409.]); Fu et al. (2010a[Fu, X.-S., Yu, X.-P., Wang, W.-M. & Lin, F. (2010a). Acta Cryst. E66, o1809.],b[Fu, X.-S., Yu, X.-P., Wang, W.-M. & Lin, F. (2010b). Acta Cryst. E66, o1744.],c[Fu, X.-S., Yu, X.-P., Wang, W.-M. & Lin, F. (2010c). Acta Cryst. E66, o1859.]).

[Scheme 1]

Experimental

Crystal data

  • C14H4Cl4FNO2

  • Mr = 378.98

  • Monoclinic, P 21 /c

  • a = 12.032 (2) Å

  • b = 13.393 (3) Å

  • c = 8.7244 (17) Å

  • β = 95.33 (3)°

  • V = 1399.8 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.86 mm−1

  • T = 113 K

  • 0.22 × 0.20 × 0.16 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. ]) Tmin = 0.833, Tmax = 0.875

  • 9870 measured reflections

  • 2462 independent reflections

  • 2120 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.085

  • S = 1.14

  • 2462 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.54 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. ]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810032575/bv2150sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032575/bv2150Isup2.hkl

checkCIF report


Comment top

The title compound is a key intermediate in the synthesis of organic electro-luminescent materials. The emission of light by organic molecules exposed to an electric field has been wide investigated in both an academic and industrial context. (Han & Kay, 2005).

The molecular structure of the title compound is illustrated in Fig. 1. In the title compound, the two rings are nearly planar, the maximum deviations being 0.005 (2) and 0.010 (2) Å, respectively, but the molecule as a whole is not planar. The dihedral angle between the benzene ring and the phthalimide plane is 68.06 (10) °, which is greater than 59.95 (4) ° found in a related compound N-(2-fluorophenyl)phthalimide (Xu et al., 2006). A short Cl···O contact of 2.914 (2) Å exists in the crystal structure.

Related literature top

The title compound is a key intermediate in the synthesis of organic electroluminescent materials; see: Han & Kay (2005). For details of the synthesis, see: Valkonen et al. (2007); Barchin et al. (2002). For related structures, see: Xu et al. (2006); Fu et al. (2010a,b,c).

Experimental top

An acetic acid solution of 4,5,6,7-tetrachlorophthalic anhydride (28.6 g, 100 mmol) and 2-fluoroaniline (9.65 ml, 100 mmol) was refluxed overnight, and then filtered. The crude produce was recrystallized from ethyl acetate.

Refinement top

H atoms were positioned geometrically and refined as riding with C—H = 0.95 Å, and Uiso(H) = 1.2Ueq(C).

Structure description top

The title compound is a key intermediate in the synthesis of organic electro-luminescent materials. The emission of light by organic molecules exposed to an electric field has been wide investigated in both an academic and industrial context. (Han & Kay, 2005).

The molecular structure of the title compound is illustrated in Fig. 1. In the title compound, the two rings are nearly planar, the maximum deviations being 0.005 (2) and 0.010 (2) Å, respectively, but the molecule as a whole is not planar. The dihedral angle between the benzene ring and the phthalimide plane is 68.06 (10) °, which is greater than 59.95 (4) ° found in a related compound N-(2-fluorophenyl)phthalimide (Xu et al., 2006). A short Cl···O contact of 2.914 (2) Å exists in the crystal structure.

The title compound is a key intermediate in the synthesis of organic electroluminescent materials; see: Han & Kay (2005). For details of the synthesis, see: Valkonen et al. (2007); Barchin et al. (2002). For related structures, see: Xu et al. (2006); Fu et al. (2010a,b,c).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecule of showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
4,5,6,7-Tetrachloro-N-(2-fluorophenyl)phthalimide top
Crystal data top
C14H4Cl4FNO2F(000) = 752
Mr = 378.98Dx = 1.798 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4679 reflections
a = 12.032 (2) Åθ = 2.3–27.9°
b = 13.393 (3) ŵ = 0.86 mm−1
c = 8.7244 (17) ÅT = 113 K
β = 95.33 (3)°Prism, colorless
V = 1399.8 (5) Å30.22 × 0.20 × 0.16 mm
Z = 4
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		2462 independent reflections
Radiation source: rotating anode2120 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.027
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.3°
ω and φ scansh = −14→13
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −15→15
Tmin = 0.833, Tmax = 0.875l = −7→10
9870 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0567P)2]
where P = (Fo2 + 2Fc2)/3
2462 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.55 e Å−3
0 restraintsΔρmin = −0.54 e Å−3
Crystal data top
C14H4Cl4FNO2V = 1399.8 (5) Å3
Mr = 378.98Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.032 (2) ŵ = 0.86 mm−1
b = 13.393 (3) ÅT = 113 K
c = 8.7244 (17) Å0.22 × 0.20 × 0.16 mm
β = 95.33 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		2462 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2120 reflections with I > 2σ(I)
Tmin = 0.833, Tmax = 0.875Rint = 0.027
9870 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.14Δρmax = 0.55 e Å−3
2462 reflectionsΔρmin = −0.54 e Å−3
199 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
xyzUiso*/Ueq
Cl10.86460 (4)0.88811 (4)0.87885 (5)0.02115 (15)
Cl21.12105 (4)0.89461 (4)0.84021 (6)0.02482 (16)
Cl31.20515 (4)0.87608 (4)0.51578 (6)0.02211 (16)
Cl41.03483 (4)0.86419 (3)0.22341 (5)0.01784 (15)
F10.59427 (10)1.01280 (10)0.21749 (17)0.0449 (4)
O10.64955 (11)0.87452 (10)0.64858 (16)0.0242 (4)
O20.77309 (11)0.84862 (10)0.17056 (15)0.0222 (3)
N10.68479 (12)0.85955 (12)0.39299 (18)0.0179 (4)
C10.71360 (15)0.86955 (14)0.5529 (2)0.0175 (4)
C20.83872 (15)0.87331 (13)0.5693 (2)0.0145 (4)
C30.91144 (15)0.88264 (13)0.6996 (2)0.0159 (4)
C41.02658 (15)0.88421 (13)0.6811 (2)0.0157 (4)
C51.06451 (15)0.87662 (12)0.5352 (2)0.0158 (4)
C60.98857 (15)0.86904 (13)0.4041 (2)0.0140 (4)
C70.87595 (15)0.86712 (13)0.4244 (2)0.0143 (4)
C80.77660 (15)0.85734 (14)0.3073 (2)0.0162 (4)
C90.57195 (15)0.85497 (15)0.3257 (2)0.0196 (4)
C100.50639 (15)0.77220 (16)0.3485 (2)0.0252 (5)
H100.53530.71800.41010.030*
C110.39733 (16)0.76994 (17)0.2793 (2)0.0315 (5)
H110.35120.71390.29470.038*
C120.35573 (17)0.84825 (18)0.1888 (3)0.0318 (5)
H120.28160.84520.14100.038*
C130.42123 (16)0.93161 (18)0.1668 (2)0.0313 (5)
H130.39260.98620.10570.038*
C140.52798 (15)0.93280 (16)0.2357 (2)0.0243 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0284 (3)0.0246 (3)0.0108 (3)−0.00137 (19)0.0036 (2)−0.00012 (18)
Cl20.0242 (3)0.0309 (3)0.0178 (3)0.0013 (2)−0.0064 (2)−0.0022 (2)
Cl30.0141 (3)0.0256 (3)0.0263 (3)0.00246 (18)0.0001 (2)−0.00010 (19)
Cl40.0185 (3)0.0213 (3)0.0145 (2)−0.00069 (17)0.00566 (19)−0.00100 (18)
F10.0410 (7)0.0357 (8)0.0559 (9)−0.0095 (6)−0.0078 (6)0.0140 (7)
O10.0213 (7)0.0350 (9)0.0178 (7)−0.0025 (6)0.0088 (6)−0.0029 (6)
O20.0208 (7)0.0331 (8)0.0127 (7)−0.0050 (6)0.0025 (5)−0.0015 (6)
N10.0134 (8)0.0252 (10)0.0156 (8)−0.0030 (6)0.0037 (7)−0.0021 (7)
C10.0196 (10)0.0162 (11)0.0166 (10)−0.0009 (7)0.0017 (8)0.0000 (7)
C20.0181 (9)0.0104 (10)0.0155 (10)−0.0004 (7)0.0035 (8)0.0016 (7)
C30.0235 (10)0.0125 (10)0.0119 (10)0.0000 (7)0.0032 (8)−0.0001 (7)
C40.0198 (10)0.0105 (10)0.0157 (10)−0.0005 (7)−0.0044 (8)0.0001 (7)
C50.0156 (9)0.0106 (10)0.0211 (11)0.0014 (7)0.0007 (8)−0.0001 (7)
C60.0187 (9)0.0107 (10)0.0132 (9)0.0001 (7)0.0044 (8)0.0012 (7)
C70.0174 (9)0.0122 (10)0.0129 (9)−0.0015 (7)0.0002 (7)0.0000 (7)
C80.0166 (9)0.0144 (10)0.0176 (10)−0.0026 (7)0.0009 (8)−0.0002 (8)
C90.0142 (9)0.0269 (12)0.0180 (10)−0.0014 (8)0.0030 (8)−0.0057 (8)
C100.0208 (10)0.0286 (13)0.0270 (11)−0.0041 (8)0.0056 (8)−0.0016 (9)
C110.0187 (10)0.0390 (14)0.0375 (13)−0.0123 (9)0.0064 (9)−0.0100 (10)
C120.0149 (10)0.0509 (16)0.0295 (13)−0.0006 (10)0.0008 (9)−0.0137 (11)
C130.0244 (11)0.0406 (14)0.0282 (12)0.0073 (10)−0.0012 (9)−0.0020 (10)
C140.0231 (10)0.0253 (12)0.0243 (11)−0.0040 (8)0.0011 (8)−0.0012 (9)
Geometric parameters (Å, º) top
Cl1—C31.7122 (19)C4—C51.396 (3)
Cl2—C41.7159 (19)C5—C61.400 (3)
Cl3—C51.7162 (18)C6—C71.383 (3)
Cl4—C61.7213 (19)C7—C81.505 (3)
F1—C141.354 (2)C9—C141.380 (3)
O1—C11.189 (2)C9—C101.385 (3)
O2—C81.195 (2)C10—C111.393 (3)
N1—C81.391 (2)C10—H100.9500
N1—C11.412 (2)C11—C121.379 (3)
N1—C91.430 (2)C11—H110.9500
C1—C21.500 (3)C12—C131.390 (3)
C2—C31.374 (3)C12—H120.9500
C2—C71.382 (3)C13—C141.367 (3)
C3—C41.410 (3)C13—H130.9500
C8—N1—C1113.51 (15)C6—C7—C8129.85 (18)
C8—N1—C9123.34 (16)O2—C8—N1125.63 (17)
C1—N1—C9123.13 (16)O2—C8—C7129.69 (17)
O1—C1—N1125.66 (17)N1—C8—C7104.68 (16)
O1—C1—C2129.89 (18)C14—C9—C10119.51 (18)
N1—C1—C2104.45 (16)C14—C9—N1120.02 (17)
C3—C2—C7121.77 (18)C10—C9—N1120.46 (18)
C3—C2—C1129.66 (18)C9—C10—C11118.8 (2)
C7—C2—C1108.56 (16)C9—C10—H10120.6
C2—C3—C4117.62 (18)C11—C10—H10120.6
C2—C3—Cl1121.41 (15)C12—C11—C10120.6 (2)
C4—C3—Cl1120.94 (15)C12—C11—H11119.7
C5—C4—C3120.75 (17)C10—C11—H11119.7
C5—C4—Cl2119.71 (14)C11—C12—C13120.64 (19)
C3—C4—Cl2119.54 (15)C11—C12—H12119.7
C4—C5—C6120.45 (17)C13—C12—H12119.7
C4—C5—Cl3119.95 (15)C14—C13—C12118.1 (2)
C6—C5—Cl3119.60 (15)C14—C13—H13121.0
C7—C6—C5118.03 (18)C12—C13—H13121.0
C7—C6—Cl4121.36 (15)F1—C14—C13119.8 (2)
C5—C6—Cl4120.61 (14)F1—C14—C9117.75 (16)
C2—C7—C6121.36 (17)C13—C14—C9122.4 (2)
C2—C7—C8108.79 (16)
C8—N1—C1—O1178.91 (18)C5—C6—C7—C20.5 (3)
C9—N1—C1—O10.6 (3)Cl4—C6—C7—C2−178.51 (13)
C8—N1—C1—C2−0.4 (2)C5—C6—C7—C8−178.53 (17)
C9—N1—C1—C2−178.80 (16)Cl4—C6—C7—C82.4 (3)
O1—C1—C2—C30.6 (3)C1—N1—C8—O2179.37 (17)
N1—C1—C2—C3179.94 (17)C9—N1—C8—O2−2.3 (3)
O1—C1—C2—C7−178.47 (19)C1—N1—C8—C7−0.1 (2)
N1—C1—C2—C70.85 (19)C9—N1—C8—C7178.26 (16)
C7—C2—C3—C4−0.9 (3)C2—C7—C8—O2−178.79 (19)
C1—C2—C3—C4−179.94 (17)C6—C7—C8—O20.4 (3)
C7—C2—C3—Cl1−178.88 (14)C2—C7—C8—N10.6 (2)
C1—C2—C3—Cl12.1 (3)C6—C7—C8—N1179.79 (18)
C2—C3—C4—C50.1 (3)C8—N1—C9—C14−67.0 (3)
Cl1—C3—C4—C5178.00 (13)C1—N1—C9—C14111.2 (2)
C2—C3—C4—Cl2−179.43 (13)C8—N1—C9—C10112.3 (2)
Cl1—C3—C4—Cl2−1.5 (2)C1—N1—C9—C10−69.5 (2)
C3—C4—C5—C61.1 (3)C14—C9—C10—C110.1 (3)
Cl2—C4—C5—C6−179.40 (13)N1—C9—C10—C11−179.17 (18)
C3—C4—C5—Cl3−178.64 (13)C9—C10—C11—C120.6 (3)
Cl2—C4—C5—Cl30.9 (2)C10—C11—C12—C13−1.0 (3)
C4—C5—C6—C7−1.4 (3)C11—C12—C13—C140.9 (3)
Cl3—C5—C6—C7178.36 (13)C12—C13—C14—F1−179.79 (18)
C4—C5—C6—Cl4177.65 (13)C12—C13—C14—C9−0.2 (3)
Cl3—C5—C6—Cl4−2.6 (2)C10—C9—C14—F1179.34 (18)
C3—C2—C7—C60.7 (3)N1—C9—C14—F1−1.4 (3)
C1—C2—C7—C6179.84 (16)C10—C9—C14—C13−0.2 (3)
C3—C2—C7—C8179.90 (16)N1—C9—C14—C13179.00 (19)
C1—C2—C7—C8−0.92 (19)

Experimental details

Crystal data
Chemical formulaC14H4Cl4FNO2
Mr378.98
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)12.032 (2), 13.393 (3), 8.7244 (17)
β (°) 95.33 (3)
V (Å3)1399.8 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.86
Crystal size (mm)0.22 × 0.20 × 0.16
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.833, 0.875
No. of measured, independent and
observed [I > 2σ(I)] reflections		9870, 2462, 2120
Rint0.027
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.085, 1.14
No. of reflections2462
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.55, −0.54

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Major Research Program of Zhejiang Province (grant No. 2008 C02007-2) and the Zhejiang Provincial Natural Science Foundation of China (grant No. Y307128).

References

First citationBarchin, B. M., Cuadro, A. M. & Alvarez-Builla, J. (2002). Synlett, 2, 343–345.  CrossRef Google Scholar
 First citationFu, X.-S., Yu, X.-P., Wang, W.-M. & Lin, F. (2010a). Acta Cryst. E66, o1809.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFu, X.-S., Yu, X.-P., Wang, W.-M. & Lin, F. (2010b). Acta Cryst. E66, o1744.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFu, X.-S., Yu, X.-P., Wang, W.-M. & Lin, F. (2010c). Acta Cryst. E66, o1859.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHan, K. J. & Kay, K. Y. (2005). J. Korean Chem. Soc. 49, 233–238.  CAS Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationValkonen, A., Lahtinen, T. & Rissanen, K. (2007). Acta Cryst. E63, o472–o473.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationXu, D., Shi, Y.-Q., Chen, B., Cheng, Y.-H. & Gao, X. (2006). Acta Cryst. E62, o408–o409.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2432
https://doi.org/10.1107/S1600536810032575
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