organic compounds
5,6-Dichloro-2-(2-hydroxyphenyl)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: muodabas@omu.edu.tr
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 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.
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).
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/S1600536808008180/hk2440sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008180/hk2440Isup2.hkl
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).
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 Uiso(H) = xUeq(C,O), where x = 1.5 for OH H and x = 1.2 for aromatic H atoms.
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).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) Å3 | 0.63 × 0.43 × 0.24 mm |
Z = 4 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2555P] where P = (Fo2 + 2Fc2)/3 |
2783 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C14H7Cl2NO3 | V = 1310.68 (7) Å3 |
Mr = 308.11 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.5993 (2) Å | µ = 0.50 mm−1 |
b = 19.4088 (5) Å | T = 296 K |
c = 9.5086 (3) Å | 0.63 × 0.43 × 0.24 mm |
β = 110.842 (2)° |
Stoe IPDSII diffractometer | 2783 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2341 reflections with I > 2σ(I) |
Tmin = 0.759, Tmax = 0.881 | Rint = 0.057 |
20050 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.21 e Å−3 |
2783 reflections | Δρmin = −0.29 e Å−3 |
182 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 > 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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2i | 0.82 | 1.90 | 2.7235 (18) | 177 |
C3—H3···O3ii | 0.93 | 2.55 | 3.397 (2) | 152 |
C13—H13···O3iii | 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. |
Experimental details
Crystal data | |
Chemical formula | C14H7Cl2NO3 |
Mr | 308.11 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.5993 (2), 19.4088 (5), 9.5086 (3) |
β (°) | 110.842 (2) |
V (Å3) | 1310.68 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.63 × 0.43 × 0.24 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.759, 0.881 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20050, 2783, 2341 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.633 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.096, 1.04 |
No. of reflections | 2783 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.29 |
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 |
O3—H3A···O2i | 0.82 | 1.90 | 2.7235 (18) | 176.6 |
C3—H3···O3ii | 0.93 | 2.55 | 3.397 (2) | 151.9 |
C13—H13···O3iii | 0.93 | 2.59 | 3.505 (2) | 167.9 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
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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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.