Ethyl 4-(4-chloro-anilino)-1-(4-chloro-phen-yl)-2-methyl-5-oxo-2,5-di-hydro-1H-pyrrole-2-carboxyl-ate.

In the title compound, C20H18Cl2N2O3, the dihedral angles between the central 2,5-di-hydro-1H-pyrrole ring and the phenyl rings are 74.87 (9) and 29.09 (9)°. Intra-molecular N-H⋯O and C-H⋯O hydrogen bonds occur. In the crystal, pairs of N-H⋯O hydrogen bonds link adjacent mol-ecules into inversion dimers and form an R 1 (2)(6)R 2 (2)(10)R 1 (2)(6) ring motif through C-H⋯O hydrogen bonds.

Related literature

For the lower toxicity of the lactam ring in comparison to lactones, see: Dembélé et al. (1992 ▶). For the importance of lactams in the synthesis of significant bio-active mol­ecules see: Nay et al. (2009 ▶); Galeazzi et al. (1996 ▶); Ghelfi et al. (1999 ▶); Hanessian et al. (1996 ▶). For the pharmacological properties of di­hydro­pyrrolo­nes, see: Bergmann & Gericke (1990 ▶); Moody & Young (1994 ▶); Nilsson et al. (1990 ▶). For a similar structure, see: Akkurt et al. (2013 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H18Cl2N2O3

M = 405.26

Triclinic,

a = 5.8319 (3) Å

b = 12.3759 (6) Å

c = 13.5707 (6) Å

α = 86.484 (2)°

β = 80.098 (2)°

γ = 78.671 (2)°

V = 945.69 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 100 K

0.48 × 0.08 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2005 ▶) T min = 0.967, T max = 0.990

15209 measured reflections

5316 independent reflections

4054 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.107

S = 1.02

5316 reflections

250 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030560/sj5367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030560/sj5367Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813030560/sj5367Isup3.cml

970696

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

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

C20H18Cl2N2O3	Z = 2
Mr = 405.26	F(000) = 420
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8319 (3) Å	Cell parameters from 6329 reflections
b = 12.3759 (6) Å	θ = 2.3–30.1°
c = 13.5707 (6) Å	µ = 0.37 mm−1
α = 86.484 (2)°	T = 100 K
β = 80.098 (2)°	Prisms, colourless
γ = 78.671 (2)°	0.48 × 0.08 × 0.03 mm
V = 945.69 (8) Å3

Bruker APEXII CCD diffractometer	5316 independent reflections
Radiation source: sealed tube	4054 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 30.5°, θmin = 2.2°
Absorption correction: numerical (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.967, Tmax = 0.990	k = −17→16
15209 measured reflections	l = −19→19

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.045	W = 1/[Σ2(FO2) + (0.044P)2 + 0.5765P] where P = (FO2 + 2FC2)/3
wR(F2) = 0.107	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.42 e Å−3
5316 reflections	Δρmin = −0.26 e Å−3
250 parameters

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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	−0.31063 (8)	0.07225 (4)	0.69233 (3)	0.0308 (1)
Cl2	1.25672 (8)	0.72550 (4)	0.02289 (3)	0.0295 (1)
O1	0.5731 (2)	0.12044 (10)	0.17897 (9)	0.0241 (3)
O2	0.6786 (2)	0.14299 (10)	0.32697 (9)	0.0236 (3)
O3	0.3146 (2)	0.43138 (9)	0.48510 (8)	0.0202 (3)
N1	0.2726 (2)	0.30149 (11)	0.37842 (10)	0.0170 (3)
N2	0.5923 (3)	0.51847 (11)	0.32002 (11)	0.0189 (4)
C1	0.7355 (4)	−0.03397 (17)	0.07524 (16)	0.0357 (6)
C2	0.7738 (3)	0.02748 (15)	0.16086 (15)	0.0289 (5)
C3	0.5515 (3)	0.17059 (13)	0.26519 (12)	0.0190 (4)
C4	0.3517 (3)	0.27458 (13)	0.27306 (12)	0.0184 (4)
C5	0.4781 (3)	0.36851 (13)	0.23366 (12)	0.0189 (4)
C6	0.4865 (3)	0.43147 (13)	0.30866 (12)	0.0170 (4)
C7	0.3497 (3)	0.39131 (13)	0.40231 (12)	0.0160 (4)
C8	0.1309 (3)	0.24248 (13)	0.45108 (11)	0.0163 (4)
C9	−0.1047 (3)	0.29019 (14)	0.48361 (13)	0.0209 (4)
C10	−0.2422 (3)	0.23718 (14)	0.55733 (13)	0.0218 (5)
C11	−0.1409 (3)	0.13768 (14)	0.59758 (12)	0.0201 (5)
C12	0.0925 (3)	0.08893 (14)	0.56566 (13)	0.0242 (5)
C13	0.2296 (3)	0.14242 (14)	0.49218 (13)	0.0212 (4)
C14	0.1474 (3)	0.26393 (15)	0.22100 (13)	0.0234 (5)
C15	0.7471 (3)	0.56641 (13)	0.24775 (12)	0.0176 (4)
C16	0.9122 (3)	0.61854 (14)	0.27971 (12)	0.0212 (4)
C17	1.0685 (3)	0.66771 (14)	0.21109 (13)	0.0237 (5)
C18	1.0587 (3)	0.66457 (13)	0.10993 (13)	0.0215 (5)
C19	0.8948 (3)	0.61546 (14)	0.07666 (13)	0.0238 (5)
C20	0.7376 (3)	0.56599 (14)	0.14567 (13)	0.0222 (5)
H1A	0.59060	−0.06430	0.09440	0.0540*
H1B	0.87100	−0.09420	0.05820	0.0540*
H1C	0.71990	0.01640	0.01710	0.0540*
H2A	0.78020	−0.02140	0.22130	0.0350*
H2B	0.92480	0.05470	0.14400	0.0350*
H2N	0.591 (3)	0.5340 (16)	0.3776 (15)	0.017 (5)*
H5	0.54190	0.38060	0.16550	0.0230*
H9	−0.17120	0.35890	0.45540	0.0250*
H10	−0.40350	0.26880	0.57980	0.0260*
H12	0.15800	0.01990	0.59360	0.0290*
H13	0.39090	0.11050	0.47010	0.0250*
H14A	0.07270	0.20340	0.25260	0.0350*
H14B	0.20690	0.24870	0.15020	0.0350*
H14C	0.03050	0.33290	0.22650	0.0350*
H16	0.91750	0.62030	0.34920	0.0250*
H17	1.18060	0.70300	0.23310	0.0280*
H19	0.88870	0.61530	0.00720	0.0290*
H20	0.62410	0.53200	0.12320	0.0270*

	U11	U22	U33	U12	U13	U23
Cl1	0.0291 (2)	0.0339 (2)	0.0272 (2)	−0.0135 (2)	0.0079 (2)	0.0061 (2)
Cl2	0.0299 (2)	0.0307 (2)	0.0238 (2)	−0.0092 (2)	0.0092 (2)	0.0045 (2)
O1	0.0237 (6)	0.0222 (6)	0.0228 (6)	−0.0007 (5)	0.0025 (5)	−0.0028 (5)
O2	0.0181 (6)	0.0245 (6)	0.0262 (6)	−0.0013 (5)	−0.0016 (5)	0.0013 (5)
O3	0.0212 (6)	0.0213 (6)	0.0175 (6)	−0.0061 (5)	0.0007 (5)	−0.0008 (4)
N1	0.0167 (6)	0.0174 (6)	0.0153 (6)	−0.0042 (5)	0.0023 (5)	0.0008 (5)
N2	0.0232 (7)	0.0200 (7)	0.0135 (7)	−0.0082 (5)	0.0011 (5)	0.0007 (5)
C1	0.0359 (11)	0.0322 (10)	0.0355 (11)	−0.0059 (8)	0.0063 (9)	−0.0096 (8)
C2	0.0246 (9)	0.0249 (9)	0.0311 (10)	0.0019 (7)	0.0063 (7)	−0.0046 (7)
C3	0.0163 (7)	0.0185 (8)	0.0205 (8)	−0.0057 (6)	0.0035 (6)	0.0012 (6)
C4	0.0185 (7)	0.0194 (8)	0.0161 (7)	−0.0049 (6)	0.0018 (6)	0.0002 (6)
C5	0.0206 (8)	0.0175 (8)	0.0167 (7)	−0.0042 (6)	0.0016 (6)	0.0031 (6)
C6	0.0142 (7)	0.0167 (7)	0.0181 (8)	−0.0015 (6)	−0.0006 (6)	0.0039 (6)
C7	0.0126 (7)	0.0156 (7)	0.0184 (7)	−0.0010 (5)	−0.0012 (6)	0.0021 (6)
C8	0.0159 (7)	0.0180 (7)	0.0145 (7)	−0.0052 (6)	0.0009 (6)	0.0007 (6)
C9	0.0171 (7)	0.0196 (8)	0.0244 (8)	−0.0018 (6)	−0.0015 (6)	0.0020 (6)
C10	0.0135 (7)	0.0252 (9)	0.0247 (8)	−0.0024 (6)	0.0012 (6)	−0.0011 (7)
C11	0.0195 (8)	0.0230 (8)	0.0172 (8)	−0.0082 (6)	0.0027 (6)	0.0013 (6)
C12	0.0234 (8)	0.0207 (8)	0.0249 (9)	−0.0020 (7)	0.0013 (7)	0.0064 (7)
C13	0.0151 (7)	0.0216 (8)	0.0232 (8)	−0.0007 (6)	0.0024 (6)	0.0039 (6)
C14	0.0208 (8)	0.0267 (9)	0.0222 (8)	−0.0041 (7)	−0.0029 (7)	−0.0010 (7)
C15	0.0192 (7)	0.0133 (7)	0.0178 (7)	−0.0016 (6)	0.0018 (6)	0.0016 (6)
C16	0.0244 (8)	0.0229 (8)	0.0154 (7)	−0.0071 (7)	0.0023 (6)	−0.0015 (6)
C17	0.0232 (8)	0.0247 (9)	0.0230 (8)	−0.0083 (7)	0.0017 (7)	−0.0016 (7)
C18	0.0222 (8)	0.0175 (8)	0.0209 (8)	−0.0032 (6)	0.0053 (6)	0.0040 (6)
C19	0.0330 (9)	0.0212 (8)	0.0151 (8)	−0.0048 (7)	0.0002 (7)	0.0037 (6)
C20	0.0272 (9)	0.0199 (8)	0.0199 (8)	−0.0073 (7)	−0.0034 (7)	0.0033 (6)

Cl1—C11	1.7431 (17)	C15—C20	1.396 (2)
Cl2—C18	1.7496 (18)	C15—C16	1.398 (2)
O1—C2	1.470 (2)	C16—C17	1.387 (2)
O1—C3	1.333 (2)	C17—C18	1.387 (2)
O2—C3	1.203 (2)	C18—C19	1.377 (3)
O3—C7	1.2245 (19)	C19—C20	1.395 (2)
N1—C4	1.463 (2)	C1—H1A	0.9800
N1—C7	1.354 (2)	C1—H1B	0.9800
N1—C8	1.434 (2)	C1—H1C	0.9800
N2—C6	1.370 (2)	C2—H2A	0.9900
N2—C15	1.401 (2)	C2—H2B	0.9900
N2—H2N	0.82 (2)	C5—H5	0.9500
C1—C2	1.498 (3)	C9—H9	0.9500
C3—C4	1.553 (2)	C10—H10	0.9500
C4—C5	1.518 (2)	C12—H12	0.9500
C4—C14	1.516 (3)	C13—H13	0.9500
C5—C6	1.332 (2)	C14—H14A	0.9800
C6—C7	1.493 (2)	C14—H14B	0.9800
C8—C9	1.391 (2)	C14—H14C	0.9800
C8—C13	1.386 (2)	C16—H16	0.9500
C9—C10	1.387 (2)	C17—H17	0.9500
C10—C11	1.381 (2)	C19—H19	0.9500
C11—C12	1.382 (3)	C20—H20	0.9500
C12—C13	1.387 (2)
C2—O1—C3	115.02 (13)	Cl2—C18—C17	119.29 (13)
C4—N1—C7	112.06 (13)	C17—C18—C19	121.37 (16)
C4—N1—C8	126.06 (13)	C18—C19—C20	119.60 (16)
C7—N1—C8	121.88 (13)	C15—C20—C19	120.01 (16)
C6—N2—C15	127.47 (14)	C2—C1—H1A	109.00
C15—N2—H2N	115.2 (13)	C2—C1—H1B	109.00
C6—N2—H2N	115.5 (13)	C2—C1—H1C	109.00
O1—C2—C1	107.00 (15)	H1A—C1—H1B	109.00
O1—C3—C4	111.43 (14)	H1A—C1—H1C	109.00
O1—C3—O2	124.67 (15)	H1B—C1—H1C	109.00
O2—C3—C4	123.77 (15)	O1—C2—H2A	110.00
N1—C4—C5	101.95 (12)	O1—C2—H2B	110.00
N1—C4—C3	109.18 (13)	C1—C2—H2A	110.00
C3—C4—C14	113.41 (14)	C1—C2—H2B	110.00
C5—C4—C14	114.95 (14)	H2A—C2—H2B	109.00
C3—C4—C5	104.40 (14)	C4—C5—H5	125.00
N1—C4—C14	112.07 (14)	C6—C5—H5	125.00
C4—C5—C6	110.04 (14)	C8—C9—H9	120.00
N2—C6—C5	136.07 (16)	C10—C9—H9	120.00
N2—C6—C7	115.09 (14)	C9—C10—H10	121.00
C5—C6—C7	108.81 (15)	C11—C10—H10	120.00
O3—C7—N1	126.42 (15)	C11—C12—H12	121.00
N1—C7—C6	106.87 (13)	C13—C12—H12	120.00
O3—C7—C6	126.70 (15)	C8—C13—H13	120.00
N1—C8—C13	120.72 (15)	C12—C13—H13	120.00
N1—C8—C9	118.79 (14)	C4—C14—H14A	109.00
C9—C8—C13	120.41 (15)	C4—C14—H14B	109.00
C8—C9—C10	119.87 (16)	C4—C14—H14C	109.00
C9—C10—C11	118.95 (16)	H14A—C14—H14B	109.00
C10—C11—C12	121.86 (16)	H14A—C14—H14C	109.00
Cl1—C11—C12	118.95 (13)	H14B—C14—H14C	109.00
Cl1—C11—C10	119.19 (14)	C15—C16—H16	120.00
C11—C12—C13	118.99 (16)	C17—C16—H16	120.00
C8—C13—C12	119.91 (16)	C16—C17—H17	120.00
C16—C15—C20	119.27 (15)	C18—C17—H17	121.00
N2—C15—C16	118.52 (15)	C18—C19—H19	120.00
N2—C15—C20	122.19 (16)	C20—C19—H19	120.00
C15—C16—C17	120.71 (15)	C15—C20—H20	120.00
C16—C17—C18	119.03 (16)	C19—C20—H20	120.00
Cl2—C18—C19	119.34 (13)
C3—O1—C2—C1	166.64 (15)	C3—C4—C5—C6	−108.42 (16)
C2—O1—C3—O2	−1.9 (2)	N1—C4—C5—C6	5.23 (18)
C2—O1—C3—C4	174.18 (13)	C4—C5—C6—C7	−4.8 (2)
C7—N1—C8—C13	−103.74 (19)	C4—C5—C6—N2	172.91 (19)
C7—N1—C4—C5	−3.72 (17)	N2—C6—C7—O3	3.8 (3)
C8—N1—C4—C5	176.48 (14)	C5—C6—C7—N1	2.39 (19)
C7—N1—C4—C14	−127.16 (15)	N2—C6—C7—N1	−175.86 (14)
C8—N1—C4—C14	53.0 (2)	C5—C6—C7—O3	−177.94 (17)
C4—N1—C8—C9	−107.33 (18)	N1—C8—C13—C12	177.09 (15)
C7—N1—C4—C3	106.33 (15)	N1—C8—C9—C10	−176.92 (15)
C8—N1—C4—C3	−73.47 (19)	C13—C8—C9—C10	−0.3 (3)
C4—N1—C7—C6	1.14 (18)	C9—C8—C13—C12	0.5 (3)
C4—N1—C7—O3	−178.53 (16)	C8—C9—C10—C11	0.4 (3)
C8—N1—C7—O3	1.3 (3)	C9—C10—C11—C12	−0.8 (3)
C4—N1—C8—C13	76.0 (2)	C9—C10—C11—Cl1	178.48 (13)
C8—N1—C7—C6	−179.05 (14)	Cl1—C11—C12—C13	−178.25 (13)
C7—N1—C8—C9	72.9 (2)	C10—C11—C12—C13	1.0 (3)
C15—N2—C6—C7	173.96 (16)	C11—C12—C13—C8	−0.9 (3)
C6—N2—C15—C16	−152.75 (18)	N2—C15—C16—C17	−179.68 (16)
C15—N2—C6—C5	−3.7 (3)	C20—C15—C16—C17	−1.2 (3)
C6—N2—C15—C20	28.8 (3)	N2—C15—C20—C19	179.60 (16)
O1—C3—C4—N1	158.36 (13)	C16—C15—C20—C19	1.2 (3)
O2—C3—C4—C14	−151.28 (17)	C15—C16—C17—C18	0.1 (3)
O1—C3—C4—C5	−93.24 (16)	C16—C17—C18—Cl2	−179.53 (13)
O2—C3—C4—C5	82.87 (19)	C16—C17—C18—C19	1.1 (3)
O2—C3—C4—N1	−25.5 (2)	Cl2—C18—C19—C20	179.51 (13)
O1—C3—C4—C14	32.62 (19)	C17—C18—C19—C20	−1.2 (3)
C14—C4—C5—C6	126.70 (16)	C18—C19—C20—C15	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.82 (2)	2.471 (19)	2.8187 (19)	107.0 (15)
N2—H2N···O3i	0.82 (2)	2.12 (2)	2.9158 (19)	164.9 (18)
C12—H12···O2ii	0.95	2.34	3.285 (2)	176
C13—H13···O2	0.95	2.41	3.142 (2)	134
C14—H14A···O2iii	0.98	2.58	3.431 (2)	146
C16—H16···O3i	0.95	2.53	3.308 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	0.82 (2)	2.471 (19)	2.8187 (19)	107.0 (15)
N2—H2N⋯O3i	0.82 (2)	2.12 (2)	2.9158 (19)	164.9 (18)
C12—H12⋯O2ii	0.95	2.34	3.285 (2)	176
C13—H13⋯O2	0.95	2.41	3.142 (2)	134
C14—H14A⋯O2iii	0.98	2.58	3.431 (2)	146
C16—H16⋯O3i	0.95	2.53	3.308 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) .