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

The title compound, C(15)H(9)ClN(2)O(2), adopts an E configuration about the C=N double bond. The mean plane of the isoindoline ring system [maximum deviation = 0.011 (2) Å] is inclined to the chloro-benzene ring by 22.62 (8)°. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming chains that propagate along [010].

Related literature

For background to and applications of amidrazones, see: Neilson et al. (1970 ▶); Lee et al. (1998 ▶); Radwan et al. (2007 ▶); Xu et al. (2009 ▶); Liu et al. (2011 ▶).

Experimental

Crystal data

C15H9ClN2O2

M = 284.69

Monoclinic,

a = 12.991 (8) Å

b = 4.808 (3) Å

c = 23.757 (11) Å

β = 120.60 (2)°

V = 1277.2 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.20 × 0.20 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.971

6727 measured reflections

2628 independent reflections

2017 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.10

2628 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044898/su2334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044898/su2334Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044898/su2334Isup3.cml

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

C15H9ClN2O2	F(000) = 584
Mr = 284.69	Dx = 1.481 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2406 reflections
a = 12.991 (8) Å	θ = 3.1–27.1°
b = 4.808 (3) Å	µ = 0.30 mm−1
c = 23.757 (11) Å	T = 293 K
β = 120.60 (2)°	Prism, yellow
V = 1277.2 (13) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	2628 independent reflections
Radiation source: fine-focus sealed tube	2017 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.942, Tmax = 0.971	k = −6→5
6727 measured reflections	l = −29→23

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.2726P] where P = (Fo2 + 2Fc2)/3
2628 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
Cl1	0.46943 (4)	0.33401 (14)	0.57225 (3)	0.0719 (2)
O1	0.37871 (11)	0.9151 (3)	0.67721 (7)	0.0559 (5)
O2	0.04114 (11)	0.5317 (3)	0.66062 (6)	0.0516 (4)
N1	0.18301 (12)	0.4921 (3)	0.60576 (7)	0.0435 (5)
N2	0.20315 (12)	0.6854 (3)	0.65344 (7)	0.0400 (5)
C1	0.23630 (16)	0.2700 (4)	0.53596 (8)	0.0417 (6)
C2	0.32867 (16)	0.1841 (4)	0.52658 (8)	0.0465 (6)
C3	0.3118 (2)	−0.0195 (4)	0.48207 (10)	0.0578 (8)
C4	0.2015 (2)	−0.1385 (4)	0.44524 (10)	0.0598 (8)
C5	0.1073 (2)	−0.0545 (4)	0.45248 (9)	0.0577 (7)
C6	0.12498 (17)	0.1482 (4)	0.49709 (9)	0.0494 (6)
C7	0.25579 (16)	0.4778 (4)	0.58538 (9)	0.0463 (6)
C8	0.29761 (14)	0.8758 (4)	0.68703 (8)	0.0400 (5)
C9	0.27449 (14)	1.0096 (3)	0.73570 (8)	0.0382 (5)
C10	0.17280 (14)	0.8941 (3)	0.73080 (8)	0.0371 (5)
C11	0.12550 (15)	0.6817 (4)	0.67897 (8)	0.0386 (5)
C12	0.13187 (16)	0.9757 (4)	0.77164 (8)	0.0427 (5)
C13	0.19584 (17)	1.1782 (4)	0.81725 (9)	0.0496 (6)
C14	0.29695 (17)	1.2934 (4)	0.82189 (9)	0.0536 (6)
C15	0.33895 (16)	1.2110 (4)	0.78112 (9)	0.0484 (6)
H3	0.37510	−0.07610	0.47700	0.0690*
H4	0.18990	−0.27670	0.41520	0.0720*
H5	0.03230	−0.13510	0.42720	0.0690*
H6	0.06100	0.20540	0.50140	0.0590*
H7	0.32090	0.59790	0.60160	0.0560*
H12	0.06370	0.89710	0.76850	0.0510*
H13	0.17040	1.23800	0.84540	0.0600*
H14	0.33820	1.43010	0.85310	0.0640*
H15	0.40740	1.28860	0.78440	0.0580*

	U11	U22	U33	U12	U13	U23
Cl1	0.0515 (3)	0.0882 (5)	0.0847 (4)	0.0060 (3)	0.0411 (3)	−0.0103 (3)
O1	0.0474 (7)	0.0648 (9)	0.0705 (9)	−0.0068 (6)	0.0410 (7)	−0.0087 (7)
O2	0.0510 (7)	0.0584 (8)	0.0576 (8)	−0.0154 (6)	0.0365 (6)	−0.0163 (6)
N1	0.0482 (8)	0.0460 (9)	0.0451 (8)	0.0008 (7)	0.0301 (7)	−0.0061 (7)
N2	0.0422 (8)	0.0420 (8)	0.0454 (8)	−0.0015 (6)	0.0293 (7)	−0.0056 (6)
C1	0.0516 (10)	0.0414 (10)	0.0415 (9)	0.0053 (8)	0.0305 (8)	0.0038 (8)
C2	0.0521 (10)	0.0507 (11)	0.0462 (10)	0.0107 (9)	0.0319 (9)	0.0065 (9)
C3	0.0763 (14)	0.0585 (13)	0.0582 (12)	0.0177 (11)	0.0485 (11)	0.0051 (10)
C4	0.0942 (16)	0.0474 (12)	0.0489 (11)	0.0047 (11)	0.0445 (12)	−0.0038 (9)
C5	0.0731 (13)	0.0559 (13)	0.0479 (11)	−0.0055 (11)	0.0335 (10)	−0.0033 (9)
C6	0.0555 (11)	0.0506 (11)	0.0502 (10)	0.0009 (9)	0.0329 (9)	−0.0018 (9)
C7	0.0483 (10)	0.0479 (11)	0.0527 (10)	−0.0014 (8)	0.0329 (9)	−0.0061 (9)
C8	0.0377 (8)	0.0412 (10)	0.0448 (9)	0.0044 (7)	0.0236 (8)	0.0034 (8)
C9	0.0358 (8)	0.0381 (9)	0.0418 (9)	0.0037 (7)	0.0205 (7)	0.0018 (7)
C10	0.0379 (8)	0.0367 (9)	0.0389 (8)	0.0025 (7)	0.0211 (7)	0.0001 (7)
C11	0.0394 (9)	0.0411 (10)	0.0423 (9)	0.0029 (8)	0.0258 (7)	0.0007 (8)
C12	0.0464 (9)	0.0444 (10)	0.0459 (9)	−0.0001 (8)	0.0297 (8)	−0.0024 (8)
C13	0.0588 (11)	0.0515 (11)	0.0453 (10)	0.0024 (9)	0.0314 (9)	−0.0060 (9)
C14	0.0556 (11)	0.0521 (12)	0.0464 (10)	−0.0036 (9)	0.0212 (9)	−0.0126 (9)
C15	0.0396 (9)	0.0494 (11)	0.0542 (11)	−0.0034 (8)	0.0224 (8)	−0.0031 (9)

Cl1—C2	1.738 (2)	C9—C15	1.372 (3)
O1—C8	1.204 (3)	C10—C11	1.472 (3)
O2—C11	1.194 (3)	C10—C12	1.380 (3)
N1—N2	1.383 (2)	C12—C13	1.377 (3)
N1—C7	1.265 (3)	C13—C14	1.377 (3)
N2—C8	1.409 (3)	C14—C15	1.390 (3)
N2—C11	1.417 (3)	C3—H3	0.9300
C1—C2	1.390 (3)	C4—H4	0.9300
C1—C6	1.388 (3)	C5—H5	0.9300
C1—C7	1.462 (3)	C6—H6	0.9300
C2—C3	1.374 (3)	C7—H7	0.9300
C3—C4	1.367 (4)	C12—H12	0.9300
C4—C5	1.380 (4)	C13—H13	0.9300
C5—C6	1.370 (3)	C14—H14	0.9300
C8—C9	1.481 (3)	C15—H15	0.9300
C9—C10	1.382 (3)
N2—N1—C7	118.91 (17)	O2—C11—C10	129.75 (19)
N1—N2—C8	130.37 (17)	N2—C11—C10	105.33 (16)
N1—N2—C11	117.57 (15)	C10—C12—C13	117.4 (2)
C8—N2—C11	111.74 (15)	C12—C13—C14	121.1 (2)
C2—C1—C6	117.38 (18)	C13—C14—C15	121.77 (18)
C2—C1—C7	121.40 (19)	C9—C15—C14	116.8 (2)
C6—C1—C7	121.2 (2)	C2—C3—H3	120.00
Cl1—C2—C1	119.77 (14)	C4—C3—H3	120.00
Cl1—C2—C3	118.74 (19)	C3—C4—H4	120.00
C1—C2—C3	121.5 (2)	C5—C4—H4	120.00
C2—C3—C4	119.7 (2)	C4—C5—H5	120.00
C3—C4—C5	120.3 (2)	C6—C5—H5	120.00
C4—C5—C6	119.6 (2)	C1—C6—H6	119.00
C1—C6—C5	121.5 (2)	C5—C6—H6	119.00
N1—C7—C1	119.14 (19)	N1—C7—H7	120.00
O1—C8—N2	126.02 (17)	C1—C7—H7	120.00
O1—C8—C9	128.90 (18)	C10—C12—H12	121.00
N2—C8—C9	105.08 (16)	C13—C12—H12	121.00
C8—C9—C10	108.94 (15)	C12—C13—H13	119.00
C8—C9—C15	129.43 (19)	C14—C13—H13	119.00
C10—C9—C15	121.62 (18)	C13—C14—H14	119.00
C9—C10—C11	108.86 (17)	C15—C14—H14	119.00
C9—C10—C12	121.37 (16)	C9—C15—H15	122.00
C11—C10—C12	129.75 (18)	C14—C15—H15	122.00
O2—C11—N2	124.92 (17)
C7—N1—N2—C8	−2.3 (3)	C3—C4—C5—C6	−0.3 (3)
C7—N1—N2—C11	−175.13 (16)	C4—C5—C6—C1	−0.7 (3)
N2—N1—C7—C1	178.75 (15)	O1—C8—C9—C10	−178.23 (19)
N1—N2—C8—O1	4.2 (3)	O1—C8—C9—C15	0.4 (3)
N1—N2—C8—C9	−175.51 (16)	N2—C8—C9—C10	1.44 (19)
C11—N2—C8—O1	177.36 (18)	N2—C8—C9—C15	−179.98 (18)
C11—N2—C8—C9	−2.33 (19)	C8—C9—C10—C11	−0.09 (19)
N1—N2—C11—O2	−3.1 (3)	C8—C9—C10—C12	178.45 (16)
N1—N2—C11—C10	176.43 (14)	C15—C9—C10—C11	−178.80 (16)
C8—N2—C11—O2	−177.28 (18)	C15—C9—C10—C12	−0.3 (3)
C8—N2—C11—C10	2.29 (19)	C8—C9—C15—C14	−178.50 (17)
C6—C1—C2—Cl1	178.49 (14)	C10—C9—C15—C14	−0.1 (3)
C6—C1—C2—C3	−2.0 (3)	C9—C10—C11—O2	178.24 (19)
C7—C1—C2—Cl1	−2.3 (2)	C9—C10—C11—N2	−1.30 (19)
C7—C1—C2—C3	177.25 (18)	C12—C10—C11—O2	−0.1 (3)
C2—C1—C6—C5	1.8 (3)	C12—C10—C11—N2	−179.67 (17)
C7—C1—C6—C5	−177.41 (18)	C9—C10—C12—C13	0.4 (3)
C2—C1—C7—N1	−159.54 (18)	C11—C10—C12—C13	178.61 (18)
C6—C1—C7—N1	19.7 (3)	C10—C12—C13—C14	−0.2 (3)
Cl1—C2—C3—C4	−179.45 (16)	C12—C13—C14—C15	−0.1 (3)
C1—C2—C3—C4	1.0 (3)	C13—C14—C15—C9	0.3 (3)
C2—C3—C4—C5	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.93	2.52	3.421 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.52	3.421 (4)	163

Symmetry code: (i) .