2-(2,6-Dichloro-benz-yl)pyrrolidine-1,3-dione.

In the title compound, C(11)H(9)Cl(2)NO(2), the dihedral anngle between the mean planes of the aromatic ring and the twisted pyrrolidinedione ring is 79.98 (9)°.

Related literature

For the synthesis, see: Duan et al. (2005 ▶). For the pharmaceutical properties of pyrrolidine-2,5-dione derivatives, see: Obniska et al. (2009 ▶).

Experimental

Crystal data

C11H9Cl2NO2

M = 258.09

Orthorhombic,

a = 4.8057 (5) Å

b = 9.4388 (8) Å

c = 23.936 (2) Å

V = 1085.74 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.58 mm−1

T = 113 K

0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.923, T max = 0.944

7528 measured reflections

2562 independent reflections

2400 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.073

S = 1.09

2562 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1017 Friedel pairs

Flack parameter: 0.01 (6)

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024970/hb5015sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024970/hb5015Isup2.hkl

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

C11H9Cl2NO2	Dx = 1.579 Mg m−3
Mr = 258.09	Melting point = 409–411 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2881 reflections
a = 4.8057 (5) Å	θ = 1.7–27.9°
b = 9.4388 (8) Å	µ = 0.58 mm−1
c = 23.936 (2) Å	T = 113 K
V = 1085.74 (18) Å3	Block, colorless
Z = 4	0.14 × 0.12 × 0.10 mm
F(000) = 528

Rigaku Saturn CCD area-detector diffractometer	2562 independent reflections
Radiation source: rotating anode	2400 reflections with I > 2σ(I)
confocal	Rint = 0.029
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 1.7°
ω and φ scans	h = −4→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
Tmin = 0.923, Tmax = 0.944	l = −30→31
7528 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0337P)2 + 0.1572P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.073	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.28 e Å−3
2562 reflections	Δρmin = −0.27 e Å−3
146 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.027 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1017 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.01 (6)

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	0.00935 (11)	−0.15827 (4)	0.039298 (15)	0.02779 (12)
Cl2	−0.01306 (10)	0.14810 (5)	0.231345 (15)	0.02661 (12)
O1	−0.4371 (3)	0.35252 (13)	0.15425 (5)	0.0256 (3)
O2	0.2345 (3)	0.17916 (13)	0.03882 (5)	0.0258 (3)
N1	−0.1077 (3)	0.23490 (14)	0.10180 (5)	0.0172 (3)
C1	−0.2311 (4)	0.35434 (18)	0.12493 (6)	0.0201 (3)
C2	−0.0631 (4)	0.48127 (18)	0.10689 (8)	0.0276 (4)
H2A	0.0514	0.5174	0.1382	0.033*
H2B	−0.1863	0.5582	0.0936	0.033*
C3	0.1211 (4)	0.42692 (18)	0.05958 (7)	0.0222 (4)
H3A	0.0520	0.4604	0.0229	0.027*
H3B	0.3156	0.4591	0.0645	0.027*
C4	0.1017 (4)	0.26745 (17)	0.06376 (6)	0.0186 (3)
C5	−0.2043 (4)	0.09082 (17)	0.11224 (6)	0.0177 (3)
H5A	−0.2735	0.0496	0.0768	0.021*
H5B	−0.3619	0.0939	0.1389	0.021*
C6	0.0205 (4)	−0.00365 (15)	0.13563 (6)	0.0160 (3)
C7	0.1336 (4)	−0.11631 (17)	0.10562 (7)	0.0193 (3)
C8	0.3417 (4)	−0.20312 (18)	0.12690 (8)	0.0255 (4)
H8	0.4149	−0.2783	0.1050	0.031*
C9	0.4416 (4)	−0.17880 (19)	0.18054 (8)	0.0283 (4)
H9	0.5851	−0.2370	0.1953	0.034*
C10	0.3327 (4)	−0.0703 (2)	0.21228 (7)	0.0253 (4)
H10	0.3987	−0.0538	0.2491	0.030*
C11	0.1251 (4)	0.01445 (17)	0.18967 (7)	0.0195 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0382 (3)	0.0230 (2)	0.02216 (19)	0.0038 (2)	−0.0022 (2)	−0.00636 (14)
Cl2	0.0287 (2)	0.0340 (2)	0.01716 (18)	0.0004 (2)	−0.00099 (17)	−0.00597 (15)
O1	0.0261 (7)	0.0286 (6)	0.0223 (5)	0.0089 (6)	0.0024 (5)	−0.0028 (5)
O2	0.0255 (7)	0.0264 (7)	0.0254 (6)	0.0043 (5)	0.0073 (5)	0.0028 (5)
N1	0.0175 (7)	0.0171 (6)	0.0171 (6)	0.0008 (6)	0.0003 (6)	−0.0001 (5)
C1	0.0224 (9)	0.0194 (8)	0.0186 (7)	0.0029 (7)	−0.0033 (6)	−0.0012 (6)
C2	0.0315 (11)	0.0185 (7)	0.0329 (9)	−0.0017 (8)	−0.0009 (8)	−0.0001 (7)
C3	0.0218 (9)	0.0207 (8)	0.0242 (8)	−0.0039 (7)	−0.0037 (7)	0.0034 (7)
C4	0.0177 (8)	0.0227 (8)	0.0155 (7)	0.0009 (7)	−0.0020 (6)	0.0018 (6)
C5	0.0188 (8)	0.0153 (7)	0.0189 (7)	−0.0005 (6)	−0.0016 (7)	−0.0002 (6)
C6	0.0141 (8)	0.0167 (7)	0.0174 (6)	−0.0022 (7)	−0.0003 (6)	0.0030 (5)
C7	0.0185 (8)	0.0183 (7)	0.0210 (7)	−0.0012 (7)	−0.0001 (7)	0.0023 (6)
C8	0.0231 (10)	0.0179 (8)	0.0354 (9)	0.0017 (7)	0.0043 (8)	0.0042 (7)
C9	0.0215 (10)	0.0245 (9)	0.0388 (10)	0.0014 (8)	−0.0007 (8)	0.0156 (7)
C10	0.0221 (10)	0.0303 (9)	0.0235 (8)	−0.0061 (8)	−0.0035 (7)	0.0109 (7)
C11	0.0172 (8)	0.0223 (8)	0.0190 (7)	−0.0021 (7)	0.0014 (7)	0.0031 (6)

Cl1—C7	1.7417 (17)	C3—H3B	0.9900
Cl2—C11	1.7400 (17)	C5—C6	1.509 (2)
O1—C1	1.213 (2)	C5—H5A	0.9900
O2—C4	1.208 (2)	C5—H5B	0.9900
N1—C1	1.389 (2)	C6—C7	1.394 (2)
N1—C4	1.391 (2)	C6—C11	1.398 (2)
N1—C5	1.459 (2)	C7—C8	1.390 (2)
C1—C2	1.508 (2)	C8—C9	1.390 (3)
C2—C3	1.526 (3)	C8—H8	0.9500
C2—H2A	0.9900	C9—C10	1.378 (3)
C2—H2B	0.9900	C9—H9	0.9500
C3—C4	1.511 (2)	C10—C11	1.389 (2)
C3—H3A	0.9900	C10—H10	0.9500
C1—N1—C4	112.99 (14)	C6—C5—H5A	109.0
C1—N1—C5	123.52 (14)	N1—C5—H5B	109.0
C4—N1—C5	123.25 (13)	C6—C5—H5B	109.0
O1—C1—N1	124.58 (16)	H5A—C5—H5B	107.8
O1—C1—C2	127.86 (16)	C7—C6—C11	115.46 (15)
N1—C1—C2	107.56 (14)	C7—C6—C5	122.61 (14)
C1—C2—C3	104.84 (14)	C11—C6—C5	121.91 (14)
C1—C2—H2A	110.8	C8—C7—C6	122.79 (16)
C3—C2—H2A	110.8	C8—C7—Cl1	116.53 (14)
C1—C2—H2B	110.8	C6—C7—Cl1	120.64 (13)
C3—C2—H2B	110.8	C7—C8—C9	119.33 (17)
H2A—C2—H2B	108.9	C7—C8—H8	120.3
C4—C3—C2	104.48 (14)	C9—C8—H8	120.3
C4—C3—H3A	110.9	C10—C9—C8	120.04 (16)
C2—C3—H3A	110.9	C10—C9—H9	120.0
C4—C3—H3B	110.9	C8—C9—H9	120.0
C2—C3—H3B	110.9	C9—C10—C11	119.09 (16)
H3A—C3—H3B	108.9	C9—C10—H10	120.5
O2—C4—N1	123.60 (15)	C11—C10—H10	120.5
O2—C4—C3	128.46 (16)	C10—C11—C6	123.25 (16)
N1—C4—C3	107.93 (14)	C10—C11—Cl2	117.94 (13)
N1—C5—C6	112.74 (14)	C6—C11—Cl2	118.80 (13)
N1—C5—H5A	109.0
C4—N1—C1—O1	171.59 (15)	N1—C5—C6—C11	69.50 (19)
C5—N1—C1—O1	−3.0 (2)	C11—C6—C7—C8	−1.7 (2)
C4—N1—C1—C2	−8.48 (18)	C5—C6—C7—C8	179.66 (15)
C5—N1—C1—C2	176.92 (14)	C11—C6—C7—Cl1	176.23 (12)
O1—C1—C2—C3	−165.92 (16)	C5—C6—C7—Cl1	−2.4 (2)
N1—C1—C2—C3	14.14 (18)	C6—C7—C8—C9	0.7 (3)
C1—C2—C3—C4	−14.26 (18)	Cl1—C7—C8—C9	−177.37 (14)
C1—N1—C4—O2	−179.73 (16)	C7—C8—C9—C10	0.6 (3)
C5—N1—C4—O2	−5.1 (3)	C8—C9—C10—C11	−0.7 (3)
C1—N1—C4—C3	−1.03 (18)	C9—C10—C11—C6	−0.5 (3)
C5—N1—C4—C3	173.59 (14)	C9—C10—C11—Cl2	178.68 (13)
C2—C3—C4—O2	−171.54 (18)	C7—C6—C11—C10	1.7 (2)
C2—C3—C4—N1	9.84 (18)	C5—C6—C11—C10	−179.73 (16)
C1—N1—C5—C6	−123.48 (16)	C7—C6—C11—Cl2	−177.52 (13)
C4—N1—C5—C6	62.46 (19)	C5—C6—C11—Cl2	1.1 (2)
N1—C5—C6—C7	−111.97 (17)