5,6-Dichloro-2-(2-hydroxy-phen-yl)-iso-indoline-1,3-dione.

In the mol-ecule of the title compound, C(14)H(7)Cl(2)NO(3), 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, inter-molecular 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 mol-ecules, generating R(2) (2)(16), R(4) (2)(19) and R(4) (4)(22) ring motifs by C(6) chains to form a three-dimensional network. A weak π-π inter-action 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

C14H7Cl2NO3

M = 308.11

Monoclinic,

a = 7.5993 (2) Å

b = 19.4088 (5) Å

c = 9.5086 (3) Å

β = 110.842 (2)°

V = 1310.68 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 296 K

0.63 × 0.43 × 0.24 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.759, T max = 0.881

20050 measured reflections

2783 independent reflections

2341 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.04

2783 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808008180/hk2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008180/hk2440Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H7Cl2NO3	F000 = 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 = 2.1–27.2º
b = 19.4088 (5) Å	µ = 0.50 mm−1
c = 9.5086 (3) Å	T = 296 K
β = 110.842 (2)º	Prism, light yellow
V = 1310.68 (7) Å3	0.63 × 0.43 × 0.24 mm
Z = 4

Stoe IPDSII diffractometer	2783 independent reflections
Monochromator: plane graphite	2341 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.057
T = 296 K	θmax = 26.7º
w–scan rotation method	θmin = 2.1º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.759, Tmax = 0.881	k = −24→24
20050 measured reflections	l = −12→12

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2555P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2783 reflections	Δρmax = 0.21 e Å−3
182 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) .