Ethyl 4-(4-chloro­anilino)-1-(4-chloro­phen­yl)-2-methyl-5-oxo-2,5-di­hydro-1H-pyrrole-2-carboxyl­ate

Akkurt, M.; Mohamed, S.K.; Elremaily, M.A.A.; Santoyo-Gonzalez, F.; Albayati, M.R.

doi:10.1107/S1600536813030560

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1761-o1762

doi:10.1107/S1600536813030560

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Ethyl 4-(4-chloroanilino)-1-(4-chlorophenyl)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate

Mehmet Akkurt,^a Shaaban K. Mohamed,^b,^c Mahmoud A.A. Elremaily,^d,^e Francisco Santoyo-Gonzalez ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, ^eDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 5 November 2013; accepted 7 November 2013; online 3 December 2013)

In the title compound, C₂₀H₁₈Cl₂N₂O₃, the dihedral angles between the central 2,5-dihydro-1H-pyrrole ring and the phenyl rings are 74.87 (9) and 29.09 (9)°. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds occur. In the crystal, pairs of N—H⋯O hydrogen bonds link adjacent molecules into inversion dimers and form an R₁²(6)R₂²(10)R₁²(6) ring motif through C—H⋯O hydrogen bonds.

CCDC reference: 970696

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_r = 405.26
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.107
S = 1.02
5316 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) x-1, y, z.

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 ).

Supporting information

CCDC reference: 970696

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813030560/sj5367sup1.cif

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

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

checkCIF report

Comment top

Lactam compounds or 2-pyrrolidinones are the aza analogues of lactones. Lactams have received relatively little attention in spite of the fact that they are potentially more effective in a pharmaceutical sense, due to the lower toxicity of the lactam ring with respect to that of the lactone (Dembélé et al., 1992). A number of substances based on the γ-lactam structure have been found in an array of natural products and act as advanced intermediates for the synthesis of many biologically important compounds such as antibiotic and anticancer agents (Nay et al., 2009; Galeazzi et al., 1996; Ghelfi et al., 1999; Hanessian et al., 1996). Also, lactams themselves exhibit interesting biological and pharmacological properties, such as psychotropic, antihypertensive and antimuscarinic activity (Bergmann & Gericke 1990; Moody & Young 1994; Nilsson et al., 1990). Based on such facts, and as an extension of our work on the production γ- lactams, we report in this study the synthesis and crystal structure of another dihydro-pyrrolone derivative.

The central 2,5-dihydro-1H-pyrrole ring (N1/C4–C7) of the title compound (I), (Fig. 1) makes dihedral angles of 74.87 (9) and 29.09 (9)° with the two phenyl rings (C8···C13 and C15···C20), respectively. All bond lengths and bond angles are normal and are similar to those found in a related compound (Akkurt et al., 2013).

In the crystal, pairs of adjacent molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), forming an inversion dimer with an R²₁(6)R²₂(10)R²₁(6) ring motif (Bernstein et al., 1995; Fig. 2). In the crystal structure, π-π and C—H···π interactions are not observed.

Related literature top

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 top

A mixture of 254 mg (2 mmol) of 4-chloroaniline and 232 mg (2 mmol) of ethyl pyruvate was taken in presence of 8 mol % of Fe₃O₄ nanoparticles in 15 ml ethanol/water (v/v) and was irradiated in a microwave for 30 minutes. The reaction progress was monitored by TLC. After completion of the reaction, the precipitated solid was filtered off, washed with water and recrystallized from ethanol. Single crystals of the title compound were obtained via slow evaporation of an ethanolic solution at room temperature.

Computing details top

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).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. A view of the hydrogen bonding (dotted lines) of the title compound in the unit cell. H atoms not involved in H bonding are omitted for clarity. [Symmetry codes: (a) -x, -y, 1 - z; (b) x, 1 + y, z; (c) 2 - x, 1 - y, -z].

Ethyl 4-(4-chloroanilino)-1-(4-chlorophenyl)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate top

Crystal data top

C₂₀H₁₈Cl₂N₂O₃	Z = 2
M_r = 405.26	F(000) = 420
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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 = (F_O² + 2F_C²)/3
wR(F²) = 0.107	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.42 e Å⁻³
5316 reflections	Δρ_min = −0.26 e Å⁻³
250 parameters

Crystal data top

C₂₀H₁₈Cl₂N₂O₃	γ = 78.671 (2)°
M_r = 405.26	V = 945.69 (8) Å³
Triclinic, P1	Z = 2
a = 5.8319 (3) Å	Mo Kα radiation
b = 12.3759 (6) Å	µ = 0.37 mm⁻¹
c = 13.5707 (6) Å	T = 100 K
α = 86.484 (2)°	0.48 × 0.08 × 0.03 mm
β = 80.098 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5316 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2005)	4054 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.990	R_int = 0.034
15209 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.42 e Å⁻³
5316 reflections	Δρ_min = −0.26 e Å⁻³
250 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

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	0.9500	2.3400	3.285 (2)	176.00
C13—H13···O2	0.9500	2.4100	3.142 (2)	134.00
C14—H14A···O2ⁱⁱⁱ	0.9800	2.5800	3.431 (2)	146.00
C16—H16···O3ⁱ	0.9500	2.5300	3.308 (2)	139.00

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z.

Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

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Volume 69| Part 12| December 2013| Pages o1761-o1762

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 4-(4-chloro­anilino)-1-(4-chloro­phen­yl)-2-methyl-5-oxo-2,5-di­hydro-1H-pyrrole-2-carboxyl­ate

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organic compounds

Ethyl 4-(4-chloroanilino)-1-(4-chlorophenyl)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate