N-(2-Chloro-phen-yl)succinimide.

In the title compound, C(10)H(8)ClNO(2), the dihedral angle between the aromatic benzene ring and the imide segment is 69.5 (1)°. In the crystal structure, mol-ecules are linked by very weak C-H⋯π inter-actions along the [001] direction.

Related literature

For our study of the effect of ring and side-chain substitutions on the structures of this class of compounds, see: Gowda et al. (2007 ▶); Saraswathi et al. (2010 ▶).

Experimental

Crystal data

C10H8ClNO2

M = 209.62

Orthorhombic,

a = 10.616 (1) Å

b = 11.191 (2) Å

c = 8.220 (1) Å

V = 976.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 299 K

0.50 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.840, T max = 0.869

2417 measured reflections

1600 independent reflections

1500 reflections with I > 2σ(I)

R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.072

S = 1.04

1600 reflections

128 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 525 Friedel pairs

Flack parameter: 0.01 (7)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010457/bx2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010457/bx2270Isup2.hkl

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

C10H8ClNO2	F(000) = 432
Mr = 209.62	Dx = 1.426 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1700 reflections
a = 10.616 (1) Å	θ = 2.6–27.7°
b = 11.191 (2) Å	µ = 0.36 mm−1
c = 8.220 (1) Å	T = 299 K
V = 976.6 (2) Å3	Prism, colourless
Z = 4	0.50 × 0.48 × 0.40 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1600 independent reflections
Radiation source: fine-focus sealed tube	1500 reflections with I > 2σ(I)
graphite	Rint = 0.008
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→13
Tmin = 0.840, Tmax = 0.869	k = −13→8
2417 measured reflections	l = −7→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1451P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.19 e Å−3
1600 reflections	Δρmin = −0.22 e Å−3
128 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.036 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 525 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.01 (7)

Experimental. (CrysAlis RED; Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 > 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	0.40098 (5)	0.22415 (4)	0.92831 (9)	0.0664 (2)
O1	0.77333 (15)	0.38146 (14)	0.8513 (2)	0.0691 (5)
O2	0.42907 (15)	0.30911 (14)	0.5374 (2)	0.0625 (4)
N1	0.60155 (12)	0.31896 (14)	0.70608 (18)	0.0386 (4)
C1	0.61026 (16)	0.19473 (17)	0.7438 (2)	0.0388 (4)
C2	0.52257 (16)	0.14047 (17)	0.8445 (3)	0.0438 (4)
C3	0.5306 (2)	0.02002 (18)	0.8789 (3)	0.0507 (5)
H3	0.4708	−0.0160	0.9455	0.061*
C4	0.6275 (2)	−0.04682 (19)	0.8141 (3)	0.0529 (5)
H4	0.6333	−0.1279	0.8375	0.063*
C5	0.71622 (19)	0.00642 (19)	0.7144 (3)	0.0540 (5)
H5	0.7817	−0.0388	0.6712	0.065*
C6	0.70742 (17)	0.12731 (18)	0.6789 (3)	0.0477 (5)
H6	0.7668	0.1631	0.6116	0.057*
C7	0.68670 (17)	0.40365 (17)	0.7621 (2)	0.0437 (4)
C8	0.65005 (18)	0.52249 (17)	0.6916 (3)	0.0481 (5)
H8A	0.7161	0.5527	0.6211	0.058*
H8B	0.6348	0.5802	0.7773	0.058*
C9	0.53041 (17)	0.49950 (18)	0.5953 (3)	0.0495 (5)
H9A	0.4599	0.5421	0.6428	0.059*
H9B	0.5405	0.5251	0.4833	0.059*
C10	0.50941 (17)	0.36713 (18)	0.6038 (3)	0.0429 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0671 (4)	0.0458 (3)	0.0864 (4)	−0.0093 (2)	0.0334 (3)	−0.0081 (3)
O1	0.0631 (9)	0.0671 (10)	0.0771 (11)	−0.0155 (8)	−0.0345 (9)	0.0026 (8)
O2	0.0574 (8)	0.0553 (9)	0.0749 (11)	−0.0085 (7)	−0.0267 (8)	0.0040 (8)
N1	0.0364 (7)	0.0401 (8)	0.0394 (9)	−0.0075 (6)	−0.0032 (7)	0.0028 (7)
C1	0.0378 (8)	0.0416 (9)	0.0370 (10)	−0.0080 (7)	−0.0070 (7)	0.0018 (8)
C2	0.0422 (9)	0.0431 (10)	0.0461 (11)	−0.0087 (8)	0.0032 (8)	−0.0038 (8)
C3	0.0550 (11)	0.0439 (10)	0.0531 (13)	−0.0117 (9)	0.0033 (10)	0.0039 (9)
C4	0.0633 (12)	0.0419 (10)	0.0535 (12)	−0.0019 (9)	−0.0108 (10)	0.0058 (10)
C5	0.0504 (11)	0.0549 (11)	0.0565 (13)	0.0114 (9)	−0.0025 (10)	0.0015 (10)
C6	0.0408 (9)	0.0567 (11)	0.0457 (11)	−0.0003 (8)	−0.0001 (9)	0.0052 (10)
C7	0.0433 (9)	0.0465 (10)	0.0414 (10)	−0.0120 (8)	0.0020 (8)	−0.0039 (8)
C8	0.0518 (10)	0.0430 (10)	0.0495 (11)	−0.0090 (9)	0.0068 (9)	−0.0039 (9)
C9	0.0443 (11)	0.0441 (10)	0.0601 (12)	0.0007 (8)	0.0014 (9)	0.0021 (10)
C10	0.0401 (9)	0.0447 (10)	0.0439 (10)	−0.0024 (8)	0.0001 (9)	0.0005 (8)

Cl1—C2	1.737 (2)	C4—H4	0.9300
O1—C7	1.202 (2)	C5—C6	1.387 (3)
O2—C10	1.203 (2)	C5—H5	0.9300
N1—C7	1.388 (2)	C6—H6	0.9300
N1—C10	1.398 (2)	C7—C8	1.502 (3)
N1—C1	1.427 (2)	C8—C9	1.519 (3)
C1—C6	1.385 (3)	C8—H8A	0.9700
C1—C2	1.386 (3)	C8—H8B	0.9700
C2—C3	1.380 (3)	C9—C10	1.500 (3)
C3—C4	1.379 (3)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.383 (3)
C7—N1—C10	113.08 (16)	C5—C6—H6	120.0
C7—N1—C1	123.41 (15)	O1—C7—N1	124.02 (19)
C10—N1—C1	123.47 (14)	O1—C7—C8	128.07 (18)
C6—C1—C2	119.44 (18)	N1—C7—C8	107.91 (16)
C6—C1—N1	119.70 (16)	C7—C8—C9	105.54 (15)
C2—C1—N1	120.86 (17)	C7—C8—H8A	110.6
C3—C2—C1	120.59 (18)	C9—C8—H8A	110.6
C3—C2—Cl1	119.42 (15)	C7—C8—H8B	110.6
C1—C2—Cl1	119.99 (15)	C9—C8—H8B	110.6
C4—C3—C2	119.79 (19)	H8A—C8—H8B	108.8
C4—C3—H3	120.1	C10—C9—C8	105.50 (16)
C2—C3—H3	120.1	C10—C9—H9A	110.6
C3—C4—C5	120.20 (19)	C8—C9—H9A	110.6
C3—C4—H4	119.9	C10—C9—H9B	110.6
C5—C4—H4	119.9	C8—C9—H9B	110.6
C4—C5—C6	119.92 (19)	H9A—C9—H9B	108.8
C4—C5—H5	120.0	O2—C10—N1	124.13 (18)
C6—C5—H5	120.0	O2—C10—C9	128.10 (19)
C1—C6—C5	120.06 (18)	N1—C10—C9	107.77 (16)
C1—C6—H6	120.0
C7—N1—C1—C6	−69.2 (2)	C4—C5—C6—C1	0.2 (3)
C10—N1—C1—C6	108.2 (2)	C10—N1—C7—O1	−179.95 (19)
C7—N1—C1—C2	110.9 (2)	C1—N1—C7—O1	−2.3 (3)
C10—N1—C1—C2	−71.7 (2)	C10—N1—C7—C8	−0.1 (2)
C6—C1—C2—C3	−0.8 (3)	C1—N1—C7—C8	177.56 (16)
N1—C1—C2—C3	179.19 (17)	O1—C7—C8—C9	−177.3 (2)
C6—C1—C2—Cl1	179.40 (15)	N1—C7—C8—C9	2.9 (2)
N1—C1—C2—Cl1	−0.7 (2)	C7—C8—C9—C10	−4.4 (2)
C1—C2—C3—C4	0.8 (3)	C7—N1—C10—O2	177.3 (2)
Cl1—C2—C3—C4	−179.36 (17)	C1—N1—C10—O2	−0.3 (3)
C2—C3—C4—C5	−0.3 (3)	C7—N1—C10—C9	−2.8 (2)
C3—C4—C5—C6	−0.2 (3)	C1—N1—C10—C9	179.55 (16)
C2—C1—C6—C5	0.2 (3)	C8—C9—C10—O2	−175.7 (2)
N1—C1—C6—C5	−179.71 (18)	C8—C9—C10—N1	4.4 (2)

D— H··· A	D— H	H··· A	D··· A	D— H··· A
C3—H3···Cg1i	0.93	2.93	3.76 (2)	149

Table 1

C—H⋯π inter­action geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D— H⋯ A	D— H	H⋯ A	D⋯ A	D— H⋯ A
C3—H3⋯Cg1i	0.93	2.93	3.76 (2)	149

Symmetry code: (i) −x + 1, −y, z + .