2-[(E)-(2,4-Dichloro-benzyl-idene)amino]-isoindoline-1,3-dione.

In the title compound, C(15)H(8)Cl(2)N(2)O(2), the mol-ecule adopts an E configuration about the central C=N double bond. The isoindoline ring is essentially planar, with a maximum deviation of 0.019 (2) Å. The dihedral angle between the isoindoline ring and the dichloro-substituted benzene ring is 6.54 (9)°. An intra-molecular C-H⋯O hydrogen bond occurs. A short Cl⋯Cl contact of 3.4027 (9) Å is present in the crystal structure. The crystal packing is further stabilized by weak C-H⋯π inter-actions.

Related literature

For the coordination ability and biological activity of Schiff bases, see: Bhunora et al. (2011 ▶); Gupta & Sutar (2008 ▶); Sridhar et al., (2001 ▶); Mladenova et al. (2002 ▶); Bharti et al. (2010 ▶); Tenorio et al. (2005 ▶); Liu et al. (1992 ▶); Hodnett & Dunn (1970 ▶).

Experimental

Crystal data

C15H8Cl2N2O2

M = 319.13

Monoclinic,

a = 8.0387 (8) Å

b = 7.6981 (8) Å

c = 22.2686 (19) Å

β = 101.828 (3)°

V = 1348.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 296 K

0.44 × 0.19 × 0.15 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.815, T max = 0.930

13900 measured reflections

3902 independent reflections

2795 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.113

S = 1.07

3902 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023063/rz2609sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023063/rz2609Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023063/rz2609Isup3.cml

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

C15H8Cl2N2O2	F(000) = 648
Mr = 319.13	Dx = 1.572 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4526 reflections
a = 8.0387 (8) Å	θ = 2.8–29.8°
b = 7.6981 (8) Å	µ = 0.49 mm−1
c = 22.2686 (19) Å	T = 296 K
β = 101.828 (3)°	Block, colourless
V = 1348.8 (2) Å3	0.44 × 0.19 × 0.15 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3902 independent reflections
Radiation source: fine-focus sealed tube	2795 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→11
Tmin = 0.815, Tmax = 0.930	k = −10→10
13900 measured reflections	l = −31→29

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0331P)2 + 0.9203P] where P = (Fo2 + 2Fc2)/3
3902 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.72877 (6)	−0.18254 (8)	0.79982 (3)	0.05067 (17)
Cl2	1.31606 (7)	−0.18842 (9)	0.72366 (3)	0.05889 (19)
O1	0.58896 (19)	0.1209 (2)	0.93934 (8)	0.0566 (5)
O2	1.08478 (17)	0.3584 (2)	1.04839 (7)	0.0457 (4)
N1	0.9657 (2)	0.1599 (2)	0.94538 (8)	0.0374 (4)
N2	0.86224 (19)	0.2180 (2)	0.98379 (7)	0.0347 (4)
C1	0.9387 (2)	−0.1149 (3)	0.81141 (9)	0.0337 (4)
C2	1.0327 (2)	−0.1710 (3)	0.76903 (9)	0.0366 (4)
H2A	0.9837	−0.2409	0.7361	0.044*
C3	1.2005 (2)	−0.1199 (3)	0.77727 (9)	0.0369 (4)
C4	1.2766 (2)	−0.0181 (3)	0.82651 (9)	0.0387 (4)
H4A	1.3906	0.0127	0.8319	0.046*
C5	1.1798 (2)	0.0371 (3)	0.86757 (9)	0.0367 (4)
H5A	1.2299	0.1064	0.9005	0.044*
C6	1.0085 (2)	−0.0087 (3)	0.86084 (8)	0.0330 (4)
C7	0.9041 (2)	0.0526 (3)	0.90345 (9)	0.0378 (4)
H7A	0.7932	0.0130	0.8997	0.045*
C8	0.6843 (2)	0.2004 (3)	0.97890 (9)	0.0366 (4)
C9	0.6452 (2)	0.3000 (3)	1.03100 (9)	0.0339 (4)
C10	0.4911 (3)	0.3240 (3)	1.04859 (10)	0.0413 (5)
H10A	0.3918	0.2728	1.0271	0.050*
C11	0.4911 (3)	0.4273 (3)	1.09946 (10)	0.0449 (5)
H11A	0.3897	0.4458	1.1125	0.054*
C12	0.6395 (3)	0.5040 (3)	1.13147 (10)	0.0491 (5)
H12A	0.6356	0.5733	1.1654	0.059*
C13	0.7941 (3)	0.4787 (3)	1.11370 (9)	0.0436 (5)
H13A	0.8937	0.5295	1.1351	0.052*
C14	0.7933 (2)	0.3755 (3)	1.06312 (9)	0.0336 (4)
C15	0.9360 (2)	0.3247 (3)	1.03399 (9)	0.0338 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0330 (2)	0.0650 (4)	0.0558 (3)	−0.0135 (2)	0.0131 (2)	−0.0105 (3)
Cl2	0.0444 (3)	0.0766 (5)	0.0621 (4)	−0.0071 (3)	0.0259 (3)	−0.0224 (3)
O1	0.0355 (8)	0.0710 (12)	0.0616 (10)	−0.0063 (8)	0.0057 (7)	−0.0274 (9)
O2	0.0290 (7)	0.0587 (10)	0.0490 (9)	−0.0036 (7)	0.0069 (6)	−0.0061 (7)
N1	0.0326 (8)	0.0425 (10)	0.0388 (9)	0.0032 (7)	0.0114 (7)	−0.0030 (7)
N2	0.0294 (7)	0.0386 (9)	0.0368 (8)	0.0007 (7)	0.0082 (6)	−0.0035 (7)
C1	0.0275 (8)	0.0357 (10)	0.0377 (10)	−0.0017 (7)	0.0060 (7)	0.0023 (8)
C2	0.0338 (9)	0.0388 (11)	0.0370 (10)	−0.0015 (8)	0.0066 (8)	−0.0031 (9)
C3	0.0322 (9)	0.0411 (11)	0.0394 (10)	0.0022 (8)	0.0123 (8)	−0.0018 (9)
C4	0.0279 (9)	0.0432 (12)	0.0446 (11)	−0.0031 (8)	0.0068 (8)	−0.0020 (9)
C5	0.0336 (9)	0.0387 (11)	0.0364 (10)	−0.0007 (8)	0.0036 (7)	−0.0033 (8)
C6	0.0319 (9)	0.0342 (10)	0.0331 (9)	0.0018 (8)	0.0071 (7)	0.0024 (8)
C7	0.0329 (9)	0.0434 (12)	0.0383 (10)	0.0007 (8)	0.0101 (8)	−0.0014 (9)
C8	0.0293 (9)	0.0395 (11)	0.0408 (10)	0.0015 (8)	0.0065 (8)	−0.0010 (9)
C9	0.0301 (9)	0.0350 (11)	0.0373 (10)	0.0013 (8)	0.0082 (7)	0.0027 (8)
C10	0.0322 (9)	0.0433 (12)	0.0499 (12)	−0.0011 (9)	0.0116 (8)	0.0036 (10)
C11	0.0407 (11)	0.0473 (13)	0.0517 (12)	0.0051 (9)	0.0216 (9)	0.0036 (10)
C12	0.0541 (13)	0.0529 (14)	0.0445 (12)	0.0032 (11)	0.0198 (10)	−0.0054 (10)
C13	0.0411 (11)	0.0498 (13)	0.0401 (11)	−0.0012 (10)	0.0084 (8)	−0.0066 (10)
C14	0.0309 (9)	0.0348 (10)	0.0354 (9)	0.0017 (8)	0.0077 (7)	0.0029 (8)
C15	0.0295 (8)	0.0372 (11)	0.0348 (9)	−0.0003 (8)	0.0071 (7)	0.0015 (8)

Cl1—C1	1.7338 (19)	C5—H5A	0.9300
Cl2—C3	1.7383 (19)	C6—C7	1.467 (3)
O1—C8	1.209 (2)	C7—H7A	0.9300
O2—C15	1.201 (2)	C8—C9	1.477 (3)
N1—C7	1.268 (3)	C9—C14	1.385 (3)
N1—N2	1.384 (2)	C9—C10	1.386 (3)
N2—C15	1.416 (3)	C10—C11	1.384 (3)
N2—C8	1.419 (2)	C10—H10A	0.9300
C1—C2	1.393 (3)	C11—C12	1.390 (3)
C1—C6	1.393 (3)	C11—H11A	0.9300
C2—C3	1.381 (3)	C12—C13	1.393 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.384 (3)	C13—C14	1.377 (3)
C4—C5	1.384 (3)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.482 (3)
C5—C6	1.399 (3)
C7—N1—N2	118.18 (16)	O1—C8—N2	125.65 (18)
N1—N2—C15	117.91 (15)	O1—C8—C9	129.07 (18)
N1—N2—C8	130.24 (16)	N2—C8—C9	105.28 (16)
C15—N2—C8	111.63 (15)	C14—C9—C10	121.44 (19)
C2—C1—C6	122.02 (17)	C14—C9—C8	108.96 (16)
C2—C1—Cl1	116.91 (15)	C10—C9—C8	129.59 (19)
C6—C1—Cl1	121.07 (15)	C11—C10—C9	117.2 (2)
C3—C2—C1	118.21 (18)	C11—C10—H10A	121.4
C3—C2—H2A	120.9	C9—C10—H10A	121.4
C1—C2—H2A	120.9	C10—C11—C12	121.30 (19)
C2—C3—C4	121.86 (18)	C10—C11—H11A	119.3
C2—C3—Cl2	117.88 (16)	C12—C11—H11A	119.3
C4—C3—Cl2	120.26 (15)	C11—C12—C13	121.2 (2)
C5—C4—C3	118.67 (18)	C11—C12—H12A	119.4
C5—C4—H4A	120.7	C13—C12—H12A	119.4
C3—C4—H4A	120.7	C14—C13—C12	117.3 (2)
C4—C5—C6	121.77 (18)	C14—C13—H13A	121.4
C4—C5—H5A	119.1	C12—C13—H13A	121.4
C6—C5—H5A	119.1	C13—C14—C9	121.60 (18)
C1—C6—C5	117.44 (17)	C13—C14—C15	129.51 (18)
C1—C6—C7	120.55 (17)	C9—C14—C15	108.90 (17)
C5—C6—C7	122.01 (18)	O2—C15—N2	124.69 (17)
N1—C7—C6	119.80 (18)	O2—C15—C14	130.08 (19)
N1—C7—H7A	120.1	N2—C15—C14	105.21 (15)
C6—C7—H7A	120.1
C7—N1—N2—C15	174.19 (18)	N2—C8—C9—C14	1.7 (2)
C7—N1—N2—C8	−11.8 (3)	O1—C8—C9—C10	1.8 (4)
C6—C1—C2—C3	0.6 (3)	N2—C8—C9—C10	−178.9 (2)
Cl1—C1—C2—C3	−179.66 (16)	C14—C9—C10—C11	0.3 (3)
C1—C2—C3—C4	1.0 (3)	C8—C9—C10—C11	−179.0 (2)
C1—C2—C3—Cl2	−179.27 (16)	C9—C10—C11—C12	0.1 (3)
C2—C3—C4—C5	−1.6 (3)	C10—C11—C12—C13	−0.4 (4)
Cl2—C3—C4—C5	178.68 (17)	C11—C12—C13—C14	0.2 (4)
C3—C4—C5—C6	0.6 (3)	C12—C13—C14—C9	0.2 (3)
C2—C1—C6—C5	−1.5 (3)	C12—C13—C14—C15	−179.5 (2)
Cl1—C1—C6—C5	178.73 (15)	C10—C9—C14—C13	−0.5 (3)
C2—C1—C6—C7	177.96 (19)	C8—C9—C14—C13	178.99 (19)
Cl1—C1—C6—C7	−1.8 (3)	C10—C9—C14—C15	179.29 (19)
C4—C5—C6—C1	0.9 (3)	C8—C9—C14—C15	−1.3 (2)
C4—C5—C6—C7	−178.58 (19)	N1—N2—C15—O2	−5.7 (3)
N2—N1—C7—C6	178.49 (17)	C8—N2—C15—O2	179.2 (2)
C1—C6—C7—N1	−174.55 (19)	N1—N2—C15—C14	175.94 (16)
C5—C6—C7—N1	4.9 (3)	C8—N2—C15—C14	0.8 (2)
N1—N2—C8—O1	3.4 (4)	C13—C14—C15—O2	1.8 (4)
C15—N2—C8—O1	177.8 (2)	C9—C14—C15—O2	−177.9 (2)
N1—N2—C8—C9	−175.91 (19)	C13—C14—C15—N2	−180.0 (2)
C15—N2—C8—C9	−1.6 (2)	C9—C14—C15—N2	0.3 (2)
O1—C8—C9—C14	−177.6 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.93	2.18	2.857 (2)	129
C2—H2A···Cg1i	0.93	2.81	3.663 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1	0.93	2.18	2.857 (2)	129
C2—H2A⋯Cg1i	0.93	2.81	3.663 (2)	153

Symmetry code: (i) .