(5E)-1-Benzyl-5-(3,3,3-tri-chloro-2-oxo-propyl-idene)pyrrolidin-2-one.

In the crystal structure of the title compound, C14H12Cl3NO2, no classical hydrogen-bonding inter-actions are observed. The methyl-ene fragments of the benzyl groups participate in non-classic hydrogen-bond inter-actions with the carbonyl O atoms of neighboring mol-ecules, generating co-operative centrosymmetric dimers with R 5 (5)(10) ring motifs. The overall mol-ecular arrangement in the unit cell seems to be highly influenced by secondary non-covalent weak C-Cl⋯π [Cl⋯Cg(phenyl ring) = 3.732 (2) Å] and C-O⋯π [O⋯Cg(pyrrolidine ring) = 2.985 (2) Å] contacts.

Related literature

For the synthesis of the title compound, see: Flores et al. (2008 ▶). For pharmacological effects, see: Van der Schyf et al. (2006 ▶). For non-classical weak contacts, see: Irving & Irving (1994 ▶); Bissantz et al. (2010 ▶). For related structures, see: Bandeira et al. (2013 ▶); de Oliveira et al. (2012 ▶); de Bittencourt et al. (2014 ▶).

Experimental

Crystal data

C14H12Cl3NO2

M = 332.60

Monoclinic,

a = 15.7822 (5) Å

b = 5.8465 (2) Å

c = 17.4107 (5) Å

β = 105.885 (1)°

V = 1545.15 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 293 K

0.83 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: gaussian (XPREP; Bruker, 2009 ▶) T min = 0.814, T max = 1.000

21458 measured reflections

5069 independent reflections

2436 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.217

S = 1.00

5069 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681400751X/zq2220sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400751X/zq2220Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400751X/zq2220Isup3.cml

CCDC reference: 740177

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H12Cl3NO2	F(000) = 680
Mr = 332.60	Dx = 1.430 Mg m−3
Monoclinic, P21/n	Melting point: 361 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.7822 (5) Å	Cell parameters from 3113 reflections
b = 5.8465 (2) Å	θ = 2.4–21.5°
c = 17.4107 (5) Å	µ = 0.59 mm−1
β = 105.885 (1)°	T = 293 K
V = 1545.15 (8) Å3	Block, yellow
Z = 4	0.83 × 0.23 × 0.19 mm

Bruker APEXII CCD diffractometer	5069 independent reflections
Radiation source: fine-focus sealed tube	2436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 31.5°, θmin = 2.7°
Absorption correction: gaussian (XPREP; Bruker, 2009)	h = −23→23
Tmin = 0.814, Tmax = 1	k = −8→3
21458 measured reflections	l = −25→25

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1095P)2 + 0.2217P] where P = (Fo2 + 2Fc2)/3
5069 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Experimental. Gaussian absorption correction based on the face-indexed crystal size

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
Cl11	−0.04344 (5)	−0.0759 (2)	0.73859 (6)	0.0958 (3)
Cl12	0.01375 (6)	0.32178 (15)	0.83385 (6)	0.0921 (3)
Cl13	0.03185 (7)	−0.11995 (17)	0.90926 (6)	0.0955 (3)
O71	0.50426 (12)	0.2290 (4)	0.95046 (11)	0.0688 (5)
N1	0.35352 (12)	0.2022 (3)	0.92101 (10)	0.0485 (5)
O21	0.13827 (13)	−0.1294 (4)	0.75824 (13)	0.0766 (6)
C9	0.30299 (15)	0.3271 (4)	1.03807 (14)	0.0517 (6)
C4	0.28593 (15)	0.0825 (4)	0.87105 (13)	0.0473 (5)
C2	0.13065 (16)	−0.0046 (4)	0.81150 (14)	0.0541 (6)
C3	0.20017 (17)	0.1159 (4)	0.86770 (14)	0.0537 (6)
H3	0.1858	0.2195	0.9027	0.064*
C8	0.34165 (19)	0.3933 (4)	0.97121 (15)	0.0573 (6)
H81	0.3035	0.5058	0.9379	0.069*
H82	0.3984	0.4653	0.9939	0.069*
C6	0.42339 (17)	−0.0584 (5)	0.85719 (15)	0.0584 (6)
H62	0.4489	−0.1974	0.8843	0.070*
H61	0.4507	−0.0263	0.8148	0.070*
C5	0.32443 (16)	−0.0833 (4)	0.82383 (14)	0.0507 (5)
H51	0.3062	−0.0455	0.7674	0.061*
H52	0.3060	−0.2384	0.8308	0.061*
C10	0.32564 (18)	0.1269 (5)	1.08009 (16)	0.0614 (7)
H10	0.3654	0.0275	1.0667	0.074*
C7	0.43644 (17)	0.1369 (4)	0.91455 (14)	0.0536 (6)
C11	0.2900 (2)	0.0712 (7)	1.14227 (18)	0.0810 (9)
H11	0.3059	−0.0653	1.1699	0.097*
C14	0.2441 (2)	0.4725 (6)	1.0591 (2)	0.0778 (8)
H14	0.2273	0.6087	1.0315	0.093*
C13	0.2094 (2)	0.4110 (8)	1.1238 (2)	0.0972 (12)
H13	0.1704	0.5088	1.1389	0.117*
C1	0.03650 (17)	0.0294 (5)	0.82250 (16)	0.0615 (6)
C12	0.2326 (2)	0.2126 (8)	1.1629 (2)	0.0930 (11)
H12	0.2089	0.1729	1.2044	0.112*

	U11	U22	U33	U12	U13	U23
Cl11	0.0520 (4)	0.1369 (8)	0.0932 (6)	−0.0116 (4)	0.0110 (4)	−0.0291 (5)
Cl12	0.0838 (6)	0.0785 (6)	0.1221 (7)	0.0163 (4)	0.0416 (5)	−0.0080 (5)
Cl13	0.0997 (7)	0.1099 (7)	0.0892 (6)	−0.0161 (5)	0.0465 (5)	0.0130 (5)
O71	0.0531 (10)	0.0804 (13)	0.0728 (11)	−0.0168 (9)	0.0169 (9)	−0.0078 (10)
N1	0.0497 (10)	0.0571 (11)	0.0417 (9)	−0.0128 (8)	0.0175 (8)	−0.0064 (8)
O21	0.0558 (11)	0.0922 (15)	0.0809 (13)	−0.0063 (10)	0.0169 (10)	−0.0388 (11)
C9	0.0454 (12)	0.0599 (14)	0.0497 (12)	−0.0087 (10)	0.0130 (10)	−0.0156 (11)
C4	0.0522 (13)	0.0517 (12)	0.0396 (11)	−0.0085 (10)	0.0155 (9)	−0.0008 (9)
C2	0.0508 (13)	0.0580 (14)	0.0547 (14)	−0.0029 (11)	0.0166 (11)	−0.0057 (11)
C3	0.0545 (13)	0.0597 (14)	0.0491 (13)	−0.0055 (11)	0.0176 (11)	−0.0090 (10)
C8	0.0633 (15)	0.0533 (13)	0.0576 (14)	−0.0138 (11)	0.0205 (12)	−0.0080 (11)
C6	0.0532 (14)	0.0696 (16)	0.0537 (14)	0.0010 (11)	0.0167 (11)	−0.0030 (12)
C5	0.0551 (13)	0.0542 (13)	0.0441 (11)	−0.0039 (10)	0.0158 (10)	−0.0027 (10)
C10	0.0568 (15)	0.0748 (17)	0.0579 (14)	−0.0009 (12)	0.0245 (12)	−0.0040 (13)
C7	0.0545 (14)	0.0640 (14)	0.0433 (12)	−0.0096 (11)	0.0150 (10)	0.0011 (10)
C11	0.088 (2)	0.101 (2)	0.0599 (17)	−0.0077 (18)	0.0312 (16)	0.0037 (16)
C14	0.0735 (19)	0.081 (2)	0.082 (2)	0.0109 (15)	0.0257 (16)	−0.0153 (16)
C13	0.075 (2)	0.140 (4)	0.089 (2)	0.013 (2)	0.0438 (19)	−0.033 (2)
C1	0.0522 (14)	0.0691 (16)	0.0661 (16)	−0.0036 (12)	0.0208 (12)	−0.0052 (13)
C12	0.088 (2)	0.131 (3)	0.074 (2)	−0.013 (2)	0.0459 (19)	−0.012 (2)

Cl11—C1	1.760 (3)	C8—H82	0.9700
Cl12—C1	1.769 (3)	C6—C7	1.494 (3)
Cl13—C1	1.764 (3)	C6—C5	1.517 (4)
O71—C7	1.208 (3)	C6—H62	0.9700
N1—C4	1.370 (3)	C6—H61	0.9700
N1—C7	1.397 (3)	C5—H51	0.9700
N1—C8	1.462 (3)	C5—H52	0.9700
O21—C2	1.212 (3)	C10—C11	1.389 (4)
C9—C10	1.375 (4)	C10—H10	0.9300
C9—C14	1.381 (4)	C11—C12	1.345 (5)
C9—C8	1.505 (3)	C11—H11	0.9300
C4—C3	1.353 (3)	C14—C13	1.426 (5)
C4—C5	1.503 (3)	C14—H14	0.9300
C2—C3	1.439 (4)	C13—C12	1.345 (6)
C2—C1	1.562 (3)	C13—H13	0.9300
C3—H3	0.9300	C12—H12	0.9300
C8—H81	0.9700
C4—N1—C7	113.14 (19)	C6—C5—H51	110.8
C4—N1—C8	124.4 (2)	C4—C5—H52	110.8
C7—N1—C8	122.2 (2)	C6—C5—H52	110.8
C10—C9—C14	118.6 (2)	H51—C5—H52	108.8
C10—C9—C8	121.9 (2)	C9—C10—C11	120.8 (3)
C14—C9—C8	119.4 (3)	C9—C10—H10	119.6
C3—C4—N1	123.4 (2)	C11—C10—H10	119.6
C3—C4—C5	128.2 (2)	O71—C7—N1	123.6 (2)
N1—C4—C5	108.4 (2)	O71—C7—C6	128.8 (2)
O21—C2—C3	126.8 (2)	N1—C7—C6	107.6 (2)
O21—C2—C1	117.9 (2)	C12—C11—C10	120.7 (4)
C3—C2—C1	115.4 (2)	C12—C11—H11	119.7
C4—C3—C2	121.8 (2)	C10—C11—H11	119.7
C4—C3—H3	119.1	C9—C14—C13	119.1 (3)
C2—C3—H3	119.1	C9—C14—H14	120.5
N1—C8—C9	114.3 (2)	C13—C14—H14	120.5
N1—C8—H81	108.7	C12—C13—C14	120.5 (3)
C9—C8—H81	108.7	C12—C13—H13	119.8
N1—C8—H82	108.7	C14—C13—H13	119.8
C9—C8—H82	108.7	C2—C1—Cl11	110.10 (18)
H81—C8—H82	107.6	C2—C1—Cl13	107.82 (19)
C7—C6—C5	105.6 (2)	Cl11—C1—Cl13	110.45 (15)
C7—C6—H62	110.6	C2—C1—Cl12	111.45 (18)
C5—C6—H62	110.6	Cl11—C1—Cl12	108.04 (16)
C7—C6—H61	110.6	Cl13—C1—Cl12	109.00 (15)
C5—C6—H61	110.6	C13—C12—C11	120.3 (3)
H62—C6—H61	108.8	C13—C12—H12	119.8
C4—C5—C6	104.88 (19)	C11—C12—H12	119.8
C4—C5—H51	110.8
C7—N1—C4—C3	179.4 (2)	C8—N1—C7—O71	1.3 (4)
C8—N1—C4—C3	−5.8 (3)	C4—N1—C7—C6	−3.7 (3)
C7—N1—C4—C5	−0.5 (3)	C8—N1—C7—C6	−178.6 (2)
C8—N1—C4—C5	174.3 (2)	C5—C6—C7—O71	−173.7 (3)
N1—C4—C3—C2	176.7 (2)	C5—C6—C7—N1	6.2 (3)
C5—C4—C3—C2	−3.4 (4)	C9—C10—C11—C12	−0.2 (5)
O21—C2—C3—C4	−6.5 (4)	C10—C9—C14—C13	0.4 (4)
C1—C2—C3—C4	172.5 (2)	C8—C9—C14—C13	−178.5 (3)
C4—N1—C8—C9	67.9 (3)	C9—C14—C13—C12	−1.0 (6)
C7—N1—C8—C9	−117.8 (2)	O21—C2—C1—Cl11	−13.2 (3)
C10—C9—C8—N1	38.3 (3)	C3—C2—C1—Cl11	167.62 (19)
C14—C9—C8—N1	−142.8 (3)	O21—C2—C1—Cl13	107.3 (3)
C3—C4—C5—C6	−175.6 (2)	C3—C2—C1—Cl13	−71.8 (3)
N1—C4—C5—C6	4.3 (2)	O21—C2—C1—Cl12	−133.1 (2)
C7—C6—C5—C4	−6.3 (2)	C3—C2—C1—Cl12	47.8 (3)
C14—C9—C10—C11	0.2 (4)	C14—C13—C12—C11	1.0 (6)
C8—C9—C10—C11	179.1 (3)	C10—C11—C12—C13	−0.4 (6)
C4—N1—C7—O71	176.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H82···O71i	0.97	2.38	3.292 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H82⋯O71i	0.97	2.38	3.292 (3)	156

Symmetry code: (i) .