5,6-Dichloro-2-(2-fluoro­phen­yl)iso­indoline-1,3-dione

Büyükgüngör, O.; Odabaşoğlu, M.

doi:10.1107/S1600536808010544

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o882

doi:10.1107/S1600536808010544

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5,6-Dichloro-2-(2-fluorophenyl)isoindoline-1,3-dione

Orhan Büyükgüngör ^a ^* and Mustafa Odabaşoğlu ^b

^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

(Received 4 April 2008; accepted 16 April 2008; online 23 April 2008)

The crystal structure of the title compound, C₁₄H₆Cl₂FNO₂, 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).

Related 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

C₁₄H₆Cl₂FNO₂
M_r = 310.11
Orthorhombic, P b c a
a = 8.0078 (3) Å
b = 27.3570 (9) Å
c = 11.5563 (5) Å
V = 2531.63 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 296 K
0.76 × 0.50 × 0.20 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.703, T_max = 0.907
31181 measured reflections
2384 independent reflections
1956 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.085
S = 1.03
2384 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ . Cg1 is the centroid of atoms C2–C7.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010544/bt2693sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010544/bt2693Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For general background, see: Hall et al. (1987); Abdel-Hafez (2004); Sena et al. (2007). For related literature, see: Loudon (2002).

Experimental top

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%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the higher occupied of the disordered sites is shown.
	Fig. 2. A partial packing diagram of (I), showing the formation of C(3) chain and π–π interactions. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) 1 - x,1 - y,1 - z; (ii) 1/2 + x, y, 3/2 - z; (iii) x - 1/2, y, 3/2 - z].
	Fig. 3. The sp² hybridization of the adjacent carbon and the overlap of unshared electrons on nitrogen with π-electron system of carbonyl groups.

5,6-Dichloro-2-(2-fluorophenyl)isoindoline-1,3-dione top

Crystal data top

C₁₄H₆Cl₂FNO₂	F(000) = 1248
M_r = 310.11	D_x = 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

Data collection top

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	R_int = 0.063
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.6°, θ_min = 1.5°
ω scan rotation method	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −33→33
T_min = 0.703, T_max = 0.907	l = −14→14
31181 measured reflections

Refinement top

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(F_o²) + (0.0471P)² + 0.3058P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2384 reflections	Δρ_max = 0.15 e Å⁻³
192 parameters	Δρ_min = −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)

Crystal data top

C₁₄H₆Cl₂FNO₂	V = 2531.63 (17) Å³
M_r = 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

Data collection top

Stoe IPDSII diffractometer	2384 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1956 reflections with I > 2σ(I)
T_min = 0.703, T_max = 0.907	R_int = 0.063
31181 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
2384 reflections	Δρ_min = −0.17 e Å⁻³
192 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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.703, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	31181, 2384, 1956
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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).

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