N-(3-Chloro-phen-yl)succinimide.

In the title compound, C(10)H(8)ClNO(2), the chloro-benzene and the essentially planar (r.m.s. deviation = 0.030 Å) pyrrolidine ring are tilted by 59.5 (1)° with respect to one another.

Related literature

For our studies on the effects of substituents on the structures of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (1999 ▶, 2007 ▶); Saraswathi et al. (2010 ▶).

Experimental

Crystal data

C10H8ClNO2

M = 209.62

Orthorhombic,

a = 12.884 (2) Å

b = 7.173 (1) Å

c = 20.805 (3) Å

V = 1922.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 293 K

0.46 × 0.12 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.849, T max = 0.968

6087 measured reflections

1755 independent reflections

1163 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.137

S = 1.33

1755 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.46 e Å−3

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 datablock(s) I, global. DOI: 10.1107/S1600536811026845/bt5570sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026845/bt5570Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026845/bt5570Isup3.cml

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

C10H8ClNO2	F(000) = 864
Mr = 209.62	Dx = 1.448 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1436 reflections
a = 12.884 (2) Å	θ = 2.8–27.8°
b = 7.173 (1) Å	µ = 0.37 mm−1
c = 20.805 (3) Å	T = 293 K
V = 1922.7 (5) Å3	Needle, colourless
Z = 8	0.46 × 0.12 × 0.09 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1755 independent reflections
Radiation source: fine-focus sealed tube	1163 reflections with I > 2σ(I)
graphite	Rint = 0.044
Rotation method data acquisition using ω scans	θmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→15
Tmin = 0.849, Tmax = 0.968	k = −6→8
6087 measured reflections	l = −25→22

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.33	w = 1/[σ2(Fo2) + (0.0157P)2 + 3.1516P] where P = (Fo2 + 2Fc2)/3
1755 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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 > 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
C1	0.1240 (3)	0.3985 (6)	0.39944 (19)	0.0406 (10)
C2	0.1122 (3)	0.2512 (6)	0.44197 (19)	0.0427 (10)
H2	0.1035	0.1300	0.4269	0.051*
C3	0.1135 (3)	0.2881 (7)	0.5070 (2)	0.0474 (12)
C4	0.1279 (3)	0.4651 (8)	0.5302 (2)	0.0572 (13)
H4	0.1292	0.4874	0.5743	0.069*
C5	0.1403 (3)	0.6090 (7)	0.4874 (2)	0.0590 (14)
H5	0.1504	0.7294	0.5028	0.071*
C6	0.1381 (3)	0.5785 (6)	0.4213 (2)	0.0489 (12)
H6	0.1459	0.6769	0.3926	0.059*
C7	0.2069 (4)	0.3968 (6)	0.2912 (2)	0.0437 (11)
C8	0.1764 (4)	0.3477 (7)	0.2235 (2)	0.0557 (13)
H8A	0.2260	0.2619	0.2047	0.067*
H8B	0.1725	0.4586	0.1970	0.067*
C9	0.0704 (4)	0.2568 (7)	0.2297 (2)	0.0600 (14)
H9A	0.0203	0.3189	0.2023	0.072*
H9B	0.0738	0.1263	0.2177	0.072*
C10	0.0405 (4)	0.2769 (6)	0.2994 (2)	0.0498 (12)
N1	0.1227 (3)	0.3623 (4)	0.33150 (16)	0.0408 (9)
O1	0.2895 (2)	0.4592 (4)	0.30949 (15)	0.0591 (9)
O2	−0.0397 (3)	0.2302 (5)	0.32476 (16)	0.0706 (10)
Cl1	0.09625 (11)	0.1056 (2)	0.56153 (6)	0.0722 (5)

	U11	U22	U33	U12	U13	U23
C1	0.033 (2)	0.048 (3)	0.041 (2)	0.002 (2)	−0.0020 (19)	−0.006 (2)
C2	0.042 (3)	0.042 (2)	0.043 (3)	0.004 (2)	−0.001 (2)	−0.006 (2)
C3	0.036 (3)	0.067 (3)	0.039 (3)	0.002 (2)	−0.001 (2)	−0.005 (2)
C4	0.042 (3)	0.085 (4)	0.044 (3)	−0.004 (3)	0.003 (2)	−0.021 (3)
C5	0.041 (3)	0.065 (3)	0.071 (3)	−0.008 (3)	0.006 (3)	−0.035 (3)
C6	0.038 (3)	0.045 (3)	0.064 (3)	−0.004 (2)	0.005 (2)	−0.008 (2)
C7	0.055 (3)	0.035 (2)	0.042 (2)	0.003 (2)	0.000 (2)	0.005 (2)
C8	0.076 (3)	0.052 (3)	0.040 (3)	0.002 (3)	−0.003 (2)	0.007 (2)
C9	0.081 (4)	0.053 (3)	0.046 (3)	−0.006 (3)	−0.018 (3)	0.003 (2)
C10	0.057 (3)	0.039 (3)	0.053 (3)	−0.003 (2)	−0.013 (3)	0.006 (2)
N1	0.044 (2)	0.040 (2)	0.0386 (19)	−0.0028 (17)	−0.0024 (17)	0.0015 (17)
O1	0.053 (2)	0.069 (2)	0.055 (2)	−0.0133 (18)	0.0055 (17)	0.0002 (17)
O2	0.057 (2)	0.087 (3)	0.068 (2)	−0.024 (2)	−0.011 (2)	0.003 (2)
Cl1	0.0824 (9)	0.0924 (10)	0.0418 (6)	0.0078 (8)	0.0035 (7)	0.0082 (7)

C1—C6	1.380 (6)	C7—O1	1.214 (5)
C1—C2	1.387 (6)	C7—N1	1.393 (5)
C1—N1	1.437 (5)	C7—C8	1.505 (6)
C2—C3	1.379 (6)	C8—C9	1.518 (7)
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.371 (6)	C8—H8B	0.9700
C3—Cl1	1.746 (5)	C9—C10	1.507 (6)
C4—C5	1.374 (7)	C9—H9A	0.9700
C4—H4	0.9300	C9—H9B	0.9700
C5—C6	1.393 (6)	C10—O2	1.208 (5)
C5—H5	0.9300	C10—N1	1.395 (5)
C6—H6	0.9300
C6—C1—C2	121.2 (4)	N1—C7—C8	108.5 (4)
C6—C1—N1	119.6 (4)	C7—C8—C9	104.9 (4)
C2—C1—N1	119.2 (4)	C7—C8—H8A	110.8
C3—C2—C1	118.6 (4)	C9—C8—H8A	110.8
C3—C2—H2	120.7	C7—C8—H8B	110.8
C1—C2—H2	120.7	C9—C8—H8B	110.8
C4—C3—C2	121.7 (4)	H8A—C8—H8B	108.8
C4—C3—Cl1	118.9 (4)	C10—C9—C8	105.7 (4)
C2—C3—Cl1	119.4 (4)	C10—C9—H9A	110.6
C3—C4—C5	118.9 (4)	C8—C9—H9A	110.6
C3—C4—H4	120.6	C10—C9—H9B	110.6
C5—C4—H4	120.6	C8—C9—H9B	110.6
C4—C5—C6	121.4 (5)	H9A—C9—H9B	108.7
C4—C5—H5	119.3	O2—C10—N1	124.2 (4)
C6—C5—H5	119.3	O2—C10—C9	127.8 (4)
C1—C6—C5	118.3 (4)	N1—C10—C9	108.0 (4)
C1—C6—H6	120.8	C7—N1—C10	112.4 (4)
C5—C6—H6	120.8	C7—N1—C1	123.3 (3)
O1—C7—N1	124.1 (4)	C10—N1—C1	124.1 (4)
O1—C7—C8	127.5 (4)
C6—C1—C2—C3	0.8 (6)	C8—C9—C10—N1	−2.7 (5)
N1—C1—C2—C3	−179.9 (4)	O1—C7—N1—C10	−175.1 (4)
C1—C2—C3—C4	−1.1 (7)	C8—C7—N1—C10	6.0 (5)
C1—C2—C3—Cl1	178.8 (3)	O1—C7—N1—C1	0.5 (6)
C2—C3—C4—C5	0.6 (7)	C8—C7—N1—C1	−178.4 (4)
Cl1—C3—C4—C5	−179.3 (3)	O2—C10—N1—C7	178.3 (4)
C3—C4—C5—C6	0.3 (7)	C9—C10—N1—C7	−2.0 (5)
C2—C1—C6—C5	0.1 (6)	O2—C10—N1—C1	2.7 (7)
N1—C1—C6—C5	−179.2 (4)	C9—C10—N1—C1	−177.6 (4)
C4—C5—C6—C1	−0.6 (7)	C6—C1—N1—C7	61.9 (5)
O1—C7—C8—C9	173.9 (4)	C2—C1—N1—C7	−117.5 (4)
N1—C7—C8—C9	−7.3 (5)	C6—C1—N1—C10	−123.0 (4)
C7—C8—C9—C10	5.9 (5)	C2—C1—N1—C10	57.7 (5)
C8—C9—C10—O2	176.9 (5)