organic compounds
5,6-Dichloro-2-(2-fluorophenyl)isoindoline-1,3-dione
aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, and bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
*Correspondence e-mail: orhanb@omu.edu.tr
The 14H6Cl2FNO2, exhibits C—H⋯π and π–π interactions, which generate C(3) chains in the [100] direction. The π–π interaction occurs between the aromatic rings of isoindoline units, with a centroid–centroid distance of 3.672 Å and an interplanar separation of 3.528 Å. The isoindoline unit is planar and inclined at an angle of 58.63 (18)° to the substituent benzene ring. The F atom is disordered over two positions, with refined occupancies of 0.669 (3) and 0.331 (3).
of the title compound, CRelated literature
For general background, see: Hall et al. (1987); Abdel-Hafez (2004); Sena et al. (2007). For related literature, see: Loudon (2002).
Experimental
Crystal data
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808010544/bt2693sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010544/bt2693Isup2.hkl
A mixture of 4,5-dichlorophthalic acid (1.175 g, 0.005 mol) and 2-fluoroaniline (0.56 g, 0.005 mol) in DMF (1.5 ml) was heated at boiling temperature 15 min. The reaction mixture added in 50 ml e thanol (95%) and crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of this mixture at room temperature (yield 80%).
The F atom is disordered over two ortho positions with refined occupancies of 0.669 (3) and 0.331 (3). H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C14H6Cl2FNO2 | F(000) = 1248 |
Mr = 310.11 | Dx = 1.622 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 31181 reflections |
a = 8.0078 (3) Å | θ = 1.5–26.2° |
b = 27.3570 (9) Å | µ = 0.52 mm−1 |
c = 11.5563 (5) Å | T = 296 K |
V = 2531.63 (17) Å3 | Prism, colorless |
Z = 8 | 0.76 × 0.50 × 0.20 mm |
Stoe IPDSII diffractometer | 2384 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1956 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.063 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.6°, θmin = 1.5° |
ω scan rotation method | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −33→33 |
Tmin = 0.703, Tmax = 0.907 | l = −14→14 |
31181 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3058P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2384 reflections | Δρmax = 0.15 e Å−3 |
192 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0107 (9) |
C14H6Cl2FNO2 | V = 2531.63 (17) Å3 |
Mr = 310.11 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.0078 (3) Å | µ = 0.52 mm−1 |
b = 27.3570 (9) Å | T = 296 K |
c = 11.5563 (5) Å | 0.76 × 0.50 × 0.20 mm |
Stoe IPDSII diffractometer | 2384 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1956 reflections with I > 2σ(I) |
Tmin = 0.703, Tmax = 0.907 | Rint = 0.063 |
31181 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.15 e Å−3 |
2384 reflections | Δρmin = −0.17 e Å−3 |
192 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 | Occ. (<1) | |
C1 | 0.28581 (19) | 0.61572 (6) | 0.53527 (14) | 0.0525 (4) | |
C2 | 0.30531 (19) | 0.56310 (6) | 0.56377 (13) | 0.0503 (4) | |
C3 | 0.2424 (2) | 0.52248 (6) | 0.50902 (14) | 0.0548 (4) | |
H3 | 0.1761 | 0.5254 | 0.4433 | 0.066* | |
C4 | 0.2809 (2) | 0.47693 (6) | 0.55490 (15) | 0.0554 (4) | |
C5 | 0.3825 (2) | 0.47286 (6) | 0.65266 (15) | 0.0578 (4) | |
C6 | 0.4455 (2) | 0.51427 (7) | 0.70638 (15) | 0.0585 (4) | |
H6 | 0.5133 | 0.5118 | 0.7715 | 0.070* | |
C7 | 0.40453 (19) | 0.55905 (6) | 0.66043 (14) | 0.0516 (4) | |
C8 | 0.4518 (2) | 0.60897 (7) | 0.69910 (14) | 0.0569 (4) | |
C9 | 0.3879 (2) | 0.69277 (6) | 0.62605 (15) | 0.0557 (4) | |
C10 | 0.3223 (3) | 0.71816 (7) | 0.71829 (17) | 0.0702 (5) | |
C11 | 0.3314 (3) | 0.76849 (8) | 0.7209 (2) | 0.0850 (6) | |
H11 | 0.2870 | 0.7857 | 0.7831 | 0.102* | |
C12 | 0.4067 (3) | 0.79318 (8) | 0.6309 (2) | 0.0867 (7) | |
H12 | 0.4126 | 0.8271 | 0.6326 | 0.104* | |
C13 | 0.4725 (3) | 0.76831 (8) | 0.5395 (2) | 0.0867 (7) | |
H13 | 0.5230 | 0.7851 | 0.4790 | 0.104* | |
C14 | 0.4637 (2) | 0.71824 (7) | 0.53769 (17) | 0.0687 (5) | |
N1 | 0.37841 (17) | 0.64082 (5) | 0.61972 (11) | 0.0540 (3) | |
O1 | 0.20978 (16) | 0.63434 (4) | 0.45785 (10) | 0.0670 (3) | |
O2 | 0.53535 (19) | 0.62065 (5) | 0.78115 (12) | 0.0813 (4) | |
Cl1 | 0.20110 (7) | 0.425557 (17) | 0.48901 (4) | 0.07471 (19) | |
Cl2 | 0.43176 (8) | 0.416515 (19) | 0.70844 (5) | 0.0847 (2) | |
F1 | 0.5355 (3) | 0.69169 (7) | 0.45401 (16) | 0.0918 (7) | 0.669 (3) |
F2 | 0.2785 (5) | 0.68818 (15) | 0.8105 (3) | 0.0846 (14) | 0.331 (3) |
H10 | 0.2721 | 0.7019 | 0.7812 | 0.102* | 0.669 (3) |
H14 | 0.5077 | 0.7027 | 0.4724 | 0.102* | 0.331 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0502 (9) | 0.0555 (9) | 0.0519 (8) | 0.0034 (7) | −0.0010 (7) | 0.0013 (7) |
C2 | 0.0466 (8) | 0.0536 (9) | 0.0508 (8) | 0.0033 (7) | 0.0030 (7) | 0.0024 (7) |
C3 | 0.0548 (9) | 0.0580 (9) | 0.0517 (9) | 0.0044 (7) | −0.0005 (7) | 0.0001 (7) |
C4 | 0.0535 (9) | 0.0547 (9) | 0.0579 (9) | 0.0009 (7) | 0.0110 (8) | −0.0015 (7) |
C5 | 0.0549 (9) | 0.0571 (10) | 0.0613 (9) | 0.0070 (7) | 0.0107 (8) | 0.0102 (8) |
C6 | 0.0530 (9) | 0.0664 (11) | 0.0559 (9) | 0.0022 (8) | −0.0015 (7) | 0.0100 (8) |
C7 | 0.0451 (8) | 0.0571 (9) | 0.0527 (8) | 0.0007 (7) | 0.0012 (7) | 0.0051 (7) |
C8 | 0.0490 (9) | 0.0633 (11) | 0.0583 (9) | −0.0074 (8) | −0.0035 (8) | 0.0073 (8) |
C9 | 0.0495 (9) | 0.0536 (9) | 0.0642 (10) | −0.0071 (7) | −0.0033 (8) | 0.0033 (8) |
C10 | 0.0716 (12) | 0.0697 (12) | 0.0694 (12) | −0.0167 (10) | 0.0057 (10) | −0.0074 (9) |
C11 | 0.0756 (14) | 0.0754 (13) | 0.1040 (17) | −0.0095 (11) | 0.0001 (12) | −0.0284 (12) |
C12 | 0.0862 (15) | 0.0553 (11) | 0.1186 (19) | −0.0149 (10) | −0.0175 (14) | 0.0007 (12) |
C13 | 0.0981 (17) | 0.0699 (13) | 0.0921 (15) | −0.0261 (12) | −0.0062 (13) | 0.0163 (11) |
C14 | 0.0676 (12) | 0.0668 (11) | 0.0717 (11) | −0.0108 (9) | 0.0053 (10) | 0.0052 (9) |
N1 | 0.0530 (8) | 0.0533 (7) | 0.0556 (7) | −0.0044 (6) | −0.0038 (6) | 0.0048 (6) |
O1 | 0.0792 (9) | 0.0590 (7) | 0.0629 (7) | 0.0081 (6) | −0.0172 (6) | 0.0035 (5) |
O2 | 0.0848 (10) | 0.0764 (9) | 0.0826 (9) | −0.0197 (7) | −0.0339 (8) | 0.0115 (7) |
Cl1 | 0.0859 (4) | 0.0561 (3) | 0.0822 (3) | −0.0074 (2) | 0.0026 (3) | −0.0062 (2) |
Cl2 | 0.0989 (4) | 0.0610 (3) | 0.0943 (4) | 0.0118 (3) | −0.0031 (3) | 0.0214 (2) |
F1 | 0.1037 (15) | 0.0859 (13) | 0.0857 (12) | −0.0125 (10) | 0.0384 (11) | 0.0034 (10) |
F2 | 0.086 (3) | 0.095 (3) | 0.073 (2) | −0.018 (2) | 0.0152 (18) | −0.0176 (18) |
C1—O1 | 1.1961 (19) | C9—C10 | 1.376 (3) |
C1—N1 | 1.405 (2) | C9—C14 | 1.377 (2) |
C1—C2 | 1.485 (2) | C9—N1 | 1.425 (2) |
C2—C3 | 1.374 (2) | C10—C11 | 1.379 (3) |
C2—C7 | 1.375 (2) | C10—F2 | 1.390 (4) |
C3—C4 | 1.389 (2) | C10—H10 | 0.942 (2) |
C3—H3 | 0.9300 | C11—C12 | 1.379 (3) |
C4—C5 | 1.396 (3) | C11—H11 | 0.9300 |
C4—Cl1 | 1.7213 (17) | C12—C13 | 1.362 (3) |
C5—C6 | 1.387 (3) | C12—H12 | 0.9300 |
C5—Cl2 | 1.7169 (17) | C13—C14 | 1.372 (3) |
C6—C7 | 1.375 (2) | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | C14—F1 | 1.339 (3) |
C7—C8 | 1.486 (2) | C14—H14 | 0.935 (2) |
C8—O2 | 1.204 (2) | F1—H14 | 0.4311 (19) |
C8—N1 | 1.395 (2) | F2—H10 | 0.509 (4) |
O1—C1—N1 | 125.46 (15) | C10—C9—N1 | 121.51 (15) |
O1—C1—C2 | 129.22 (15) | C14—C9—N1 | 119.33 (16) |
N1—C1—C2 | 105.32 (13) | C9—C10—C11 | 120.04 (19) |
C3—C2—C7 | 121.37 (15) | C9—C10—F2 | 113.1 (2) |
C3—C2—C1 | 130.02 (15) | C11—C10—F2 | 125.8 (2) |
C7—C2—C1 | 108.60 (14) | C9—C10—H10 | 121.51 (19) |
C2—C3—C4 | 117.92 (16) | C11—C10—H10 | 118.4 (2) |
C2—C3—H3 | 121.0 | C10—C11—C12 | 119.7 (2) |
C4—C3—H3 | 121.0 | C10—C11—H11 | 120.1 |
C3—C4—C5 | 120.63 (16) | C12—C11—H11 | 120.1 |
C3—C4—Cl1 | 118.77 (14) | C13—C12—C11 | 120.6 (2) |
C5—C4—Cl1 | 120.61 (13) | C13—C12—H12 | 119.7 |
C6—C5—C4 | 120.61 (15) | C11—C12—H12 | 119.7 |
C6—C5—Cl2 | 118.79 (14) | C12—C13—C14 | 119.4 (2) |
C4—C5—Cl2 | 120.60 (14) | C12—C13—H13 | 120.3 |
C7—C6—C5 | 117.91 (16) | C14—C13—H13 | 120.3 |
C7—C6—H6 | 121.0 | F1—C14—C13 | 122.1 (2) |
C5—C6—H6 | 121.0 | F1—C14—C9 | 116.75 (17) |
C6—C7—C2 | 121.55 (16) | C13—C14—C9 | 121.1 (2) |
C6—C7—C8 | 129.94 (15) | C13—C14—H14 | 116.5 (2) |
C2—C7—C8 | 108.50 (14) | C9—C14—H14 | 122.33 (19) |
O2—C8—N1 | 125.90 (17) | C8—N1—C1 | 111.95 (13) |
O2—C8—C7 | 128.49 (16) | C8—N1—C9 | 124.52 (14) |
N1—C8—C7 | 105.61 (14) | C1—N1—C9 | 123.45 (14) |
C10—C9—C14 | 119.16 (17) | ||
O1—C1—C2—C3 | 0.3 (3) | N1—C9—C10—C11 | −179.04 (18) |
N1—C1—C2—C3 | −179.36 (16) | C14—C9—C10—F2 | −168.5 (2) |
O1—C1—C2—C7 | 179.79 (17) | N1—C9—C10—F2 | 11.8 (3) |
N1—C1—C2—C7 | 0.13 (17) | C9—C10—C11—C12 | −0.1 (3) |
C7—C2—C3—C4 | 0.5 (2) | F2—C10—C11—C12 | 167.6 (3) |
C1—C2—C3—C4 | 179.97 (15) | C10—C11—C12—C13 | −0.2 (4) |
C2—C3—C4—C5 | −0.9 (2) | C11—C12—C13—C14 | −0.1 (4) |
C2—C3—C4—Cl1 | 179.09 (12) | C12—C13—C14—F1 | −175.6 (2) |
C3—C4—C5—C6 | 0.6 (3) | C12—C13—C14—C9 | 0.7 (3) |
Cl1—C4—C5—C6 | −179.39 (13) | C10—C9—C14—F1 | 175.55 (19) |
C3—C4—C5—Cl2 | −179.33 (13) | N1—C9—C14—F1 | −4.7 (3) |
Cl1—C4—C5—Cl2 | 0.7 (2) | C10—C9—C14—C13 | −1.0 (3) |
C4—C5—C6—C7 | 0.1 (2) | N1—C9—C14—C13 | 178.76 (19) |
Cl2—C5—C6—C7 | −179.98 (12) | O2—C8—N1—C1 | −178.75 (17) |
C5—C6—C7—C2 | −0.5 (2) | C7—C8—N1—C1 | 1.21 (18) |
C5—C6—C7—C8 | 179.55 (16) | O2—C8—N1—C9 | −1.9 (3) |
C3—C2—C7—C6 | 0.2 (2) | C7—C8—N1—C9 | 178.08 (14) |
C1—C2—C7—C6 | −179.39 (14) | O1—C1—N1—C8 | 179.45 (16) |
C3—C2—C7—C8 | −179.87 (15) | C2—C1—N1—C8 | −0.86 (17) |
C1—C2—C7—C8 | 0.59 (18) | O1—C1—N1—C9 | 2.5 (3) |
C6—C7—C8—O2 | −1.2 (3) | C2—C1—N1—C9 | −177.77 (14) |
C2—C7—C8—O2 | 178.87 (17) | C10—C9—N1—C8 | −62.0 (2) |
C6—C7—C8—N1 | 178.88 (16) | C14—C9—N1—C8 | 118.29 (19) |
C2—C7—C8—N1 | −1.10 (18) | C10—C9—N1—C1 | 114.5 (2) |
C14—C9—C10—C11 | 0.7 (3) | C14—C9—N1—C1 | −65.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cg1i | 0.93 | 2.99 | 3.844 (4) | 153 |
Symmetry code: (i) x+1/2, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C14H6Cl2FNO2 |
Mr | 310.11 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 8.0078 (3), 27.3570 (9), 11.5563 (5) |
V (Å3) | 2531.63 (17) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.76 × 0.50 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.703, 0.907 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31181, 2384, 1956 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.085, 1.03 |
No. of reflections | 2384 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.17 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cg1i | 0.93 | 2.994 | 3.844 (4) | 152.6 |
Symmetry code: (i) x+1/2, y, −z+3/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).
References
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Phthalimide derivatives have various biological activities (Hall et al., 1987; 1987; Abdel-Hafez, 2004; Sena et al. 2007). In view of the importance of the N-arylphthalimides, we herein report the results of title compound 5,6-dichloro-2-(2-fluorophenyl)isoindoline-1,3-dione, (I).
The molecule of (I) is built up from a 5,6-dichlorophthalimide unit connected to a o-fluorophenyl group through an nitrogen atom (Fig. 1). The isoindoline ring (atoms N1/C1–C8) is almost planar the largest deviation from the mean plane being 0.027 (2) Å for atom C1. The dihedral angle between the fluorophenyl ring and the mean plane of the isoindoline part is 58.63 (18)°. In (I), the crystal packing is stabilized by C6—H6···π (Table 1) interactions. The C1—N1 and C8—N1 bonds are 1.406 (2) and 1.394 (2)Å, respectively. These C—N bond lengths are shorter than C—N single bond (C—N = 1.47 Å; Loudon, 2002). This reflects both the sp2 hybridization of the adjacent carbon and the overlap of unshared electrons on nitrogen with π-electron system of carbonyl groups (Fig. 3). The π–π interaction occurs between the aromatic rings (C2–C7) of isoindoline moieties at (x; y; z) and (1 - x; 1 - y; 1 - z) sites with the centroid-centroid distance of 3.672 Å and an interplanar separation of 3.528 Å.