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

In the mol­ecule of the title compound, C₁₄H₇Cl₂NO₃, the phthalimide ring system is virtually planar, with a dihedral angle between the fused five- and six-membered rings of 4.02 (3)°. In the crystal structure, inter­molecular C—H...O and O—H...O hydrogen bonds and C—Cl...O close contacts [Cl...O = 3.0123 (13) Å and C—Cl...O = 171.14 (7)°] link the mol­ecules, generating R₂²(16), R₄²(19) and R₄⁴(22) ring motifs by C(6) chains to form a three-dimensional network. A weak π–π inter­action between the six-membered rings of the phthalimide ring systems further stabilizes the structure, with a centroid–centroid distance of 3.666 (3) Å and an interplanar separation of 3.568 Å.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.096
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.63 mm
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O1      ..       3.01 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Phthalimide derivatives have been gaining considerable interest since 1979, when Chapman et al. tested the hypolipidemic activity of 23 N-substituted phthalimide derivatives (Chapman et al., 1979). Later on, Hall and co-workers reported the antihyperlipidemic activity of phthalimide analogs in rodents and also the same activity was found by the administration of ortho-(N-phthalimido) acetophenone in sprague dawley rats (Hall et al., 1983; 1987). In 2001, Srivastava et al. reported hypolipidemic activity in α-D-mannopyranosides containing phthalimidomethyl function as aglycone (Srivastava et al., 2001). There are other interesting biological aspects of these compounds which have been reviewed in 2003 (Cechinel et al., 2003). A recent paper cites the synthesis and anticonvulsant behavior of N-substituted phthalimides (Abdel-Hafez, 2004). Besides, certain phthalimide derivatives are synthetically important, and can be transformed to other useful products (Antunes et al., 2003). In 2007, Sena et al. prepared ten N-arylaminomethyl-arylaminomethyl- and two [1,2,4-triazol-3- and 4-yl]phthalimides that these imides are potential candidates for biological evaluations (Sena et al., 2007). In view of the importance of the N-arylphthalimides, we herein report the crystal structure of the title compound, (I).

The molecule of (I), (Fig. 1), is built up from a phthalimide unit connected to a o-hydroxyphenyl group through a nitrogen atom. Rings A (C2-C7), B (C1/C2/C7/C8/N1) and C (C9-C14) are, of course, planar. The dihedral angles between them are A/B = 4.02 (3)°, A/C = 75.55 (3)° and B/C = 75.13 (3)°. So, rings A and B are also nearly coplanar. Ring C is oriented with respect to the coplanar ring system at a dihedral angle of 75.37 (3)°.

In the crystal structure, intermolecular C-H···O and O-H···O hydrogen bonds (Table 1) and C-Cl···O close contacts [Cl2ⁱ···O1ⁱⁱ = 3.0123 (13) Å and C5-Cl2ⁱ···O1ⁱⁱ = 171.14 (7)°; symmetry codes: (i) x, 3/2 - y, z - 1/2 and (ii) x + 1, 3/2 - y, z + 1/2] link the molecules, generating R₂²(16) (Fig. 3), R₄²(19) (Fig. 4) and R₄⁴(22) (Fig. 5) ring motifs by C(6) chains (Fig. 2) (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, in which they may be effective in the stabilization of the structure. A weak π···π interaction between the A rings, at x, y, z and 1 - x, 1 - y, 2 - z, further stabilizes the structure, with a centroid-centroid distance of 3.666 (3) Å and plane-plane separation of 3.568 Å.

Related literature

For general background, see: Chapman et al. (1979); Hall et al. (1983, 1987); Srivastava et al. (2001); Cechinel et al. (2003); Abdel-Hafez (2004); Antunes et al. (2003); Sena et al. (2007). For ring motif details, see: Bernstein et al. (1995); Etter (1990).

S2. Experimental

A mixture of 4,5-dichlorophthalic acid (1.175 g, 5 mmol) and 2-aminophenol (0.545 g, 20 mmol) in DMF (1.5 ml) was heated at boiling temperature for 15 min, and then ethanol (50 ml, 95%) was added. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of the mixture at room temperature (yield; 80%, m.p. 546-548 K).

S3. Refinement

H atoms were positioned geometrically, with O-H = 0.82 Å (for OH) and C-H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms with U_iso(H) = xU_eq(C,O), where x = 1.5 for OH H and x = 1.2 for aromatic H atoms.

Computing details

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

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of (I), showing the formation of C(6) chain [symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z]. H atoms not involved in hydrogen bondings have been omitted for clarity.
	Fig. 3. A partial packing diagram of (I), showing the formation of centro- symmetric R2^2(16) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry code: (i) x + 1/2, 1 - y, 1 - z]. H atoms not involved in hydrogen bondings have been omitted for clarity.
	Fig. 4. A partial packing diagram of (I), showing the formation of R2^2(16) and R4^2(19) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x + 1/2, 1 - y, 1 - z; (ii) -x, 1 - y, 1 - z; (iii) x - 1, y, z]. H atoms not involved in hydrogen bondings have been omitted for clarity.
	Fig. 5. A partial packing diagram of (I), showing the formation of R4^4(22) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x, 3/2 - y, z - 1/2; (ii) x + 1, 3/2 - y, z + 1/2; (iii) x, 3/2 - y, z + 1/2].

5,6-dichloro-2-(2-hydroxyphenyl)isoindoline-1,3-dione

Crystal data

C14H7Cl2NO3	F(000) = 624
Mr = 308.11	Dx = 1.561 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20050 reflections
a = 7.5993 (2) Å	θ = 2.1–27.2°
b = 19.4088 (5) Å	µ = 0.50 mm^−1
c = 9.5086 (3) Å	T = 296 K
β = 110.842 (2)°	Prism, light yellow
V = 1310.68 (7) Å^3	0.63 × 0.43 × 0.24 mm
Z = 4

Data collection

Stoe IPDSII diffractometer	2783 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2341 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.057
Detector resolution: 6.67 pixels mm^-1	θmax = 26.7°, θmin = 2.1°
w–scan rotation method	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
Tmin = 0.759, Tmax = 0.881	l = −12→12
20050 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0491P)^2 + 0.2555P] where P = (Fo^2 + 2Fc^2)/3
2783 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.80274 (8)	0.37446 (3)	1.02115 (6)	0.07009 (18)
Cl2	0.94040 (7)	0.51106 (3)	1.20351 (5)	0.06418 (17)
O1	0.26937 (18)	0.49684 (6)	0.49490 (13)	0.0517 (3)
O2	0.47116 (19)	0.69592 (7)	0.75853 (16)	0.0587 (3)
O3	0.40599 (18)	0.69007 (7)	0.39975 (18)	0.0624 (4)
H3A	0.4209	0.7246	0.3554	0.094*
N1	0.33154 (18)	0.60578 (7)	0.60028 (15)	0.0420 (3)
C1	0.3563 (2)	0.53405 (8)	0.59612 (17)	0.0398 (3)
C2	0.5079 (2)	0.51681 (8)	0.74085 (17)	0.0392 (3)
C3	0.5789 (2)	0.45386 (9)	0.79893 (18)	0.0458 (4)
H3	0.5389	0.4135	0.7440	0.055*
C4	0.7133 (2)	0.45279 (10)	0.94342 (19)	0.0471 (4)
C5	0.7747 (2)	0.51343 (10)	1.02414 (18)	0.0480 (4)
C6	0.7042 (2)	0.57666 (10)	0.96318 (18)	0.0482 (4)
H6	0.7463	0.6173	1.0162	0.058*
C7	0.5688 (2)	0.57720 (9)	0.82043 (17)	0.0411 (3)
C8	0.4593 (2)	0.63491 (9)	0.73015 (19)	0.0433 (4)
C9	0.1835 (2)	0.64372 (8)	0.49155 (18)	0.0424 (4)
C10	0.2248 (2)	0.68665 (9)	0.3911 (2)	0.0467 (4)
C11	0.0805 (3)	0.72369 (10)	0.2877 (2)	0.0589 (5)
H11	0.1058	0.7522	0.2185	0.071*
C12	−0.1002 (3)	0.71844 (11)	0.2873 (3)	0.0682 (6)
H12	−0.1962	0.7440	0.2187	0.082*
C13	−0.1400 (3)	0.67573 (12)	0.3875 (3)	0.0683 (6)
H13	−0.2625	0.6724	0.3864	0.082*
C14	0.0020 (3)	0.63797 (11)	0.4894 (2)	0.0562 (5)
H14	−0.0247	0.6087	0.5565	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0715 (3)	0.0663 (3)	0.0640 (3)	0.0148 (2)	0.0136 (2)	0.0208 (2)
Cl2	0.0489 (2)	0.0998 (4)	0.0362 (2)	0.0005 (2)	0.00566 (17)	0.0018 (2)
O1	0.0567 (7)	0.0453 (7)	0.0417 (6)	−0.0052 (5)	0.0037 (5)	−0.0066 (5)
O2	0.0618 (8)	0.0423 (7)	0.0678 (8)	−0.0033 (6)	0.0181 (6)	−0.0142 (6)
O3	0.0524 (7)	0.0550 (8)	0.0860 (10)	0.0091 (6)	0.0323 (7)	0.0242 (7)
N1	0.0434 (7)	0.0367 (7)	0.0412 (7)	−0.0020 (5)	0.0095 (6)	−0.0002 (5)
C1	0.0419 (8)	0.0395 (8)	0.0372 (8)	−0.0037 (6)	0.0131 (6)	−0.0015 (6)
C2	0.0397 (7)	0.0433 (8)	0.0339 (7)	−0.0042 (6)	0.0122 (6)	−0.0022 (6)
C3	0.0488 (9)	0.0427 (9)	0.0434 (8)	−0.0011 (7)	0.0134 (7)	−0.0002 (7)
C4	0.0448 (8)	0.0557 (10)	0.0418 (8)	0.0044 (7)	0.0165 (7)	0.0089 (7)
C5	0.0398 (8)	0.0694 (12)	0.0341 (7)	−0.0010 (8)	0.0122 (6)	−0.0010 (8)
C6	0.0443 (8)	0.0584 (11)	0.0391 (8)	−0.0062 (7)	0.0114 (7)	−0.0101 (7)
C7	0.0399 (8)	0.0443 (9)	0.0388 (8)	−0.0035 (6)	0.0136 (6)	−0.0057 (6)
C8	0.0420 (8)	0.0426 (9)	0.0453 (8)	−0.0053 (6)	0.0155 (7)	−0.0073 (7)
C9	0.0401 (8)	0.0377 (8)	0.0450 (8)	0.0004 (6)	0.0096 (7)	−0.0021 (6)
C10	0.0447 (8)	0.0387 (8)	0.0551 (10)	0.0038 (7)	0.0160 (7)	0.0014 (7)
C11	0.0621 (11)	0.0437 (10)	0.0633 (11)	0.0079 (8)	0.0129 (9)	0.0098 (8)
C12	0.0504 (11)	0.0565 (12)	0.0786 (14)	0.0129 (9)	−0.0007 (10)	−0.0018 (10)
C13	0.0374 (9)	0.0718 (13)	0.0878 (15)	−0.0009 (9)	0.0126 (9)	−0.0096 (12)
C14	0.0462 (9)	0.0581 (11)	0.0640 (11)	−0.0077 (8)	0.0191 (8)	−0.0053 (9)

Geometric parameters (Å, º)

O3—H3A	0.8200	C8—O2	1.211 (2)
C1—O1	1.1967 (19)	C8—N1	1.391 (2)
C1—N1	1.407 (2)	C9—C14	1.376 (2)
C1—C2	1.485 (2)	C9—C10	1.385 (2)
C2—C3	1.370 (2)	C9—N1	1.431 (2)
C2—C7	1.382 (2)	C10—O3	1.351 (2)
C3—C4	1.390 (2)	C10—C11	1.385 (2)
C3—H3	0.9300	C11—C12	1.375 (3)
C4—C5	1.392 (3)	C11—H11	0.9300
C4—Cl1	1.7213 (18)	C12—C13	1.375 (3)
C5—C6	1.381 (3)	C12—H12	0.9300
C5—Cl2	1.7229 (17)	C13—C14	1.377 (3)
C6—C7	1.381 (2)	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.475 (2)
C10—O3—H3A	109.5	C6—C7—C8	130.28 (15)
C8—N1—C1	111.65 (13)	C2—C7—C8	108.41 (14)
C8—N1—C9	123.59 (13)	O2—C8—N1	124.64 (16)
C1—N1—C9	124.56 (13)	O2—C8—C7	129.15 (16)
O1—C1—N1	125.34 (15)	N1—C8—C7	106.20 (13)
O1—C1—C2	129.33 (15)	C14—C9—C10	120.68 (16)
N1—C1—C2	105.33 (13)	C14—C9—N1	119.67 (16)
C3—C2—C7	121.90 (15)	C10—C9—N1	119.64 (14)
C3—C2—C1	129.71 (15)	O3—C10—C11	123.37 (17)
C7—C2—C1	108.32 (14)	O3—C10—C9	117.63 (15)
C2—C3—C4	117.19 (16)	C11—C10—C9	119.00 (16)
C2—C3—H3	121.4	C12—C11—C10	120.09 (19)
C4—C3—H3	121.4	C12—C11—H11	120.0
C3—C4—C5	121.12 (16)	C10—C11—H11	120.0
C3—C4—Cl1	118.46 (14)	C13—C12—C11	120.52 (18)
C5—C4—Cl1	120.42 (13)	C13—C12—H12	119.7
C6—C5—C4	121.06 (15)	C11—C12—H12	119.7
C6—C5—Cl2	118.48 (14)	C12—C13—C14	119.85 (18)
C4—C5—Cl2	120.46 (14)	C12—C13—H13	120.1
C7—C6—C5	117.47 (16)	C14—C13—H13	120.1
C7—C6—H6	121.3	C9—C14—C13	119.84 (19)
C5—C6—H6	121.3	C9—C14—H14	120.1
C6—C7—C2	121.24 (16)	C13—C14—H14	120.1
O1—C1—C2—C3	−4.3 (3)	C14—C9—C10—O3	179.76 (17)
N1—C1—C2—C3	175.38 (16)	N1—C9—C10—O3	0.7 (2)
O1—C1—C2—C7	178.66 (16)	C14—C9—C10—C11	−0.2 (3)
N1—C1—C2—C7	−1.70 (17)	N1—C9—C10—C11	−179.21 (16)
C7—C2—C3—C4	1.2 (2)	O3—C10—C11—C12	−178.91 (19)
C1—C2—C3—C4	−175.57 (16)	C9—C10—C11—C12	1.0 (3)
C2—C3—C4—C5	−1.0 (3)	C10—C11—C12—C13	−1.0 (3)
C2—C3—C4—Cl1	178.97 (12)	C11—C12—C13—C14	0.1 (3)
C3—C4—C5—C6	0.0 (3)	C10—C9—C14—C13	−0.7 (3)
Cl1—C4—C5—C6	179.98 (13)	N1—C9—C14—C13	178.34 (17)
C3—C4—C5—Cl2	179.64 (13)	C12—C13—C14—C9	0.7 (3)
Cl1—C4—C5—Cl2	−0.3 (2)	O2—C8—N1—C1	177.64 (16)
C4—C5—C6—C7	0.9 (2)	C7—C8—N1—C1	−3.01 (17)
Cl2—C5—C6—C7	−178.74 (13)	O2—C8—N1—C9	−7.3 (3)
C5—C6—C7—C2	−0.8 (2)	C7—C8—N1—C9	172.01 (14)
C5—C6—C7—C8	175.66 (16)	O1—C1—N1—C8	−177.39 (15)
C3—C2—C7—C6	−0.3 (2)	C2—C1—N1—C8	2.95 (17)
C1—C2—C7—C6	177.09 (15)	O1—C1—N1—C9	7.6 (3)
C3—C2—C7—C8	−177.42 (15)	C2—C1—N1—C9	−172.02 (14)
C1—C2—C7—C8	−0.07 (17)	C14—C9—N1—C8	−102.12 (19)
C6—C7—C8—O2	4.3 (3)	C10—C9—N1—C8	76.9 (2)
C2—C7—C8—O2	−178.86 (17)	C14—C9—N1—C1	72.3 (2)
C6—C7—C8—N1	−174.99 (17)	C10—C9—N1—C1	−108.70 (18)
C2—C7—C8—N1	1.84 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2^i	0.82	1.90	2.7235 (18)	177
C3—H3···O3^ii	0.93	2.55	3.397 (2)	152
C13—H13···O3^iii	0.93	2.59	3.505 (2)	168

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.