Ethyl 4-anilino-2-methyl-5-oxo-1-phenyl-2,5-di-hydro-1H-pyrrole-2-carboxyl-ate.

In the title compound, C20H20N2O3, the central 2,5-di-hydro-1H-pyrrole ring [r.m.s. deviation = 0.014 (1) Å] is oriented at dihedral angles of 77.81 (6) and 25.33 (6)°, respectively, to the attached phenyl ring and the aniline phenyl ring. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked through pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(10) ring motif. Two weak C-H⋯π inter-actions are also observed.

Related literature

For the synthesis of pyrrolone compounds, see: Shiraki et al. (1996 ▶). For the biological activity of lactams, see: Alvi et al. (1998 ▶); Li et al. (2002 ▶); Mase et al. (1999 ▶); Wiedhopf et al. (1973 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H20N2O3

M = 336.38

Triclinic,

a = 5.9071 (6) Å

b = 11.3474 (12) Å

c = 14.1716 (14) Å

α = 111.467 (2)°

β = 101.113 (3)°

γ = 95.328 (3)°

V = 853.45 (15) Å3

Z = 2

Cu Kα radiation

μ = 0.72 mm−1

T = 100 K

0.34 × 0.29 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.783, T max = 0.860

18887 measured reflections

3367 independent reflections

3156 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.04

3367 reflections

232 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536813030390/is5318sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030390/is5318Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030390/is5318Isup3.cml

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

C20H20N2O3	Z = 2
Mr = 336.38	F(000) = 356
Triclinic, P1	Dx = 1.309 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.9071 (6) Å	Cell parameters from 9891 reflections
b = 11.3474 (12) Å	θ = 3.5–72.5°
c = 14.1716 (14) Å	µ = 0.72 mm−1
α = 111.467 (2)°	T = 100 K
β = 101.113 (3)°	Cubs, colourless
γ = 95.328 (3)°	0.34 × 0.29 × 0.21 mm
V = 853.45 (15) Å3

Bruker APEXII CCD diffractometer	3367 independent reflections
Radiation source: sealed tube	3156 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 72.6°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.783, Tmax = 0.860	k = −14→14
18887 measured reflections	l = −17→17

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.3108P] WHERE P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.32 e Å−3
3367 reflections	Δρmin = −0.17 e Å−3
232 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
O1	0.25546 (15)	0.15386 (9)	0.65884 (6)	0.0278 (3)
O2	0.56211 (15)	0.05034 (9)	0.64918 (7)	0.0284 (3)
O3	0.76449 (14)	−0.06561 (7)	0.91641 (6)	0.0245 (2)
N1	0.46752 (16)	−0.03089 (9)	0.80378 (7)	0.0188 (2)
N2	0.88879 (16)	0.20496 (9)	1.01844 (7)	0.0198 (3)
C1	0.0420 (2)	0.20985 (14)	0.52705 (10)	0.0347 (4)
C2	0.2691 (2)	0.17212 (13)	0.56318 (10)	0.0321 (4)
C3	0.41016 (19)	0.09001 (10)	0.69110 (8)	0.0202 (3)
C4	0.37187 (18)	0.07904 (10)	0.79249 (8)	0.0185 (3)
C5	0.53286 (19)	0.19157 (10)	0.88320 (8)	0.0186 (3)
C6	0.69734 (18)	0.14945 (10)	0.93602 (8)	0.0174 (3)
C7	0.65363 (18)	0.00576 (10)	0.88708 (8)	0.0179 (3)
C8	0.38731 (19)	−0.16263 (10)	0.73392 (8)	0.0195 (3)
C9	0.5140 (2)	−0.22001 (12)	0.66212 (11)	0.0326 (4)
C10	0.4452 (2)	−0.34902 (13)	0.59739 (12)	0.0386 (4)
C11	0.2505 (2)	−0.42071 (11)	0.60400 (10)	0.0279 (3)
C12	0.1241 (2)	−0.36303 (11)	0.67556 (9)	0.0262 (3)
C13	0.1920 (2)	−0.23334 (11)	0.74107 (9)	0.0241 (3)
C14	0.11531 (19)	0.07087 (11)	0.79771 (9)	0.0235 (3)
C15	0.97223 (19)	0.33611 (10)	1.07830 (8)	0.0189 (3)
C16	1.2078 (2)	0.37409 (11)	1.13371 (9)	0.0229 (3)
C17	1.2957 (2)	0.50213 (12)	1.19811 (10)	0.0258 (3)
C18	1.1522 (2)	0.59446 (11)	1.20871 (10)	0.0263 (3)
C19	0.9195 (2)	0.55647 (11)	1.15397 (10)	0.0273 (3)
C20	0.8280 (2)	0.42848 (11)	1.08897 (9)	0.0233 (3)
H1A	−0.08820	0.14030	0.51190	0.0520*
H1B	0.04340	0.22560	0.46360	0.0520*
H1C	0.02220	0.28840	0.58200	0.0520*
H2A	0.28960	0.09150	0.50930	0.0390*
H2B	0.40280	0.24060	0.57730	0.0390*
H2N	0.981 (3)	0.1504 (14)	1.0297 (11)	0.025 (3)*
H5	0.51940	0.27930	0.90030	0.0220*
H9	0.64740	−0.17100	0.65730	0.0390*
H10	0.53200	−0.38860	0.54820	0.0460*
H11	0.20380	−0.50930	0.55940	0.0340*
H12	−0.00960	−0.41220	0.68000	0.0310*
H13	0.10520	−0.19370	0.79020	0.0290*
H14A	0.01820	0.00030	0.73480	0.0350*
H14B	0.06470	0.15210	0.80210	0.0350*
H14C	0.09850	0.05490	0.85970	0.0350*
H16	1.30760	0.31200	1.12720	0.0270*
H17	1.45580	0.52720	1.23550	0.0310*
H18	1.21320	0.68220	1.25280	0.0320*
H19	0.82040	0.61890	1.16090	0.0330*
H20	0.66770	0.40400	1.05190	0.0280*

	U11	U22	U33	U12	U13	U23
O1	0.0344 (5)	0.0343 (5)	0.0224 (4)	0.0158 (4)	0.0085 (4)	0.0168 (4)
O2	0.0282 (4)	0.0362 (5)	0.0246 (4)	0.0117 (4)	0.0100 (3)	0.0131 (4)
O3	0.0252 (4)	0.0189 (4)	0.0263 (4)	0.0053 (3)	−0.0017 (3)	0.0091 (3)
N1	0.0187 (4)	0.0161 (4)	0.0194 (4)	0.0038 (3)	0.0006 (4)	0.0064 (4)
N2	0.0209 (5)	0.0171 (4)	0.0189 (5)	0.0058 (4)	0.0009 (4)	0.0057 (4)
C1	0.0423 (8)	0.0358 (7)	0.0282 (6)	0.0081 (6)	0.0000 (6)	0.0190 (6)
C2	0.0427 (7)	0.0380 (7)	0.0222 (6)	0.0129 (6)	0.0085 (5)	0.0176 (5)
C3	0.0206 (5)	0.0180 (5)	0.0183 (5)	0.0022 (4)	0.0009 (4)	0.0053 (4)
C4	0.0191 (5)	0.0172 (5)	0.0192 (5)	0.0051 (4)	0.0031 (4)	0.0074 (4)
C5	0.0210 (5)	0.0162 (5)	0.0178 (5)	0.0041 (4)	0.0048 (4)	0.0057 (4)
C6	0.0188 (5)	0.0170 (5)	0.0165 (5)	0.0036 (4)	0.0059 (4)	0.0057 (4)
C7	0.0177 (5)	0.0184 (5)	0.0178 (5)	0.0038 (4)	0.0048 (4)	0.0069 (4)
C8	0.0199 (5)	0.0171 (5)	0.0191 (5)	0.0033 (4)	−0.0004 (4)	0.0069 (4)
C9	0.0248 (6)	0.0221 (6)	0.0442 (8)	0.0011 (5)	0.0142 (5)	0.0034 (5)
C10	0.0354 (7)	0.0237 (6)	0.0481 (8)	0.0039 (5)	0.0205 (6)	−0.0003 (6)
C11	0.0303 (6)	0.0177 (5)	0.0285 (6)	0.0010 (5)	0.0018 (5)	0.0043 (5)
C12	0.0291 (6)	0.0229 (6)	0.0245 (6)	−0.0031 (5)	0.0035 (5)	0.0104 (5)
C13	0.0298 (6)	0.0232 (6)	0.0197 (5)	0.0022 (5)	0.0065 (5)	0.0092 (5)
C14	0.0189 (5)	0.0255 (6)	0.0277 (6)	0.0056 (4)	0.0056 (4)	0.0121 (5)
C15	0.0225 (5)	0.0175 (5)	0.0166 (5)	0.0032 (4)	0.0052 (4)	0.0066 (4)
C16	0.0217 (5)	0.0221 (6)	0.0242 (6)	0.0055 (4)	0.0051 (4)	0.0081 (5)
C17	0.0211 (5)	0.0247 (6)	0.0275 (6)	−0.0004 (4)	0.0036 (5)	0.0080 (5)
C18	0.0302 (6)	0.0174 (5)	0.0271 (6)	−0.0003 (5)	0.0055 (5)	0.0059 (5)
C19	0.0302 (6)	0.0191 (6)	0.0306 (6)	0.0077 (5)	0.0056 (5)	0.0076 (5)
C20	0.0219 (5)	0.0207 (6)	0.0238 (6)	0.0048 (4)	0.0024 (4)	0.0063 (5)

O1—C2	1.4601 (16)	C16—C17	1.3857 (19)
O1—C3	1.3317 (15)	C17—C18	1.3920 (19)
O2—C3	1.2025 (15)	C18—C19	1.3825 (18)
O3—C7	1.2237 (14)	C19—C20	1.3904 (18)
N1—C4	1.4639 (16)	C1—H1A	0.9800
N1—C7	1.3530 (14)	C1—H1B	0.9800
N1—C8	1.4296 (15)	C1—H1C	0.9800
N2—C6	1.3638 (14)	C2—H2A	0.9900
N2—C15	1.3985 (16)	C2—H2B	0.9900
N2—H2N	0.898 (17)	C5—H5	0.9500
C1—C2	1.4991 (19)	C9—H9	0.9500
C3—C4	1.5434 (15)	C10—H10	0.9500
C4—C5	1.5130 (16)	C11—H11	0.9500
C4—C14	1.5274 (16)	C12—H12	0.9500
C5—C6	1.3418 (16)	C13—H13	0.9500
C6—C7	1.4938 (17)	C14—H14A	0.9800
C8—C9	1.3851 (17)	C14—H14B	0.9800
C8—C13	1.3848 (17)	C14—H14C	0.9800
C9—C10	1.383 (2)	C16—H16	0.9500
C10—C11	1.3845 (19)	C17—H17	0.9500
C11—C12	1.3825 (17)	C18—H18	0.9500
C12—C13	1.3912 (18)	C19—H19	0.9500
C15—C20	1.3953 (17)	C20—H20	0.9500
C15—C16	1.3994 (16)
C2—O1—C3	116.61 (9)	C2—C1—H1A	110.00
C4—N1—C7	112.22 (10)	C2—C1—H1B	109.00
C4—N1—C8	125.67 (9)	C2—C1—H1C	109.00
C7—N1—C8	122.05 (10)	H1A—C1—H1B	109.00
C6—N2—C15	127.95 (10)	H1A—C1—H1C	109.00
C15—N2—H2N	116.7 (10)	H1B—C1—H1C	109.00
C6—N2—H2N	114.9 (10)	O1—C2—H2A	111.00
O1—C2—C1	106.07 (10)	O1—C2—H2B	111.00
O1—C3—O2	124.92 (11)	C1—C2—H2A	110.00
O2—C3—C4	125.00 (11)	C1—C2—H2B	111.00
O1—C3—C4	110.04 (9)	H2A—C2—H2B	109.00
N1—C4—C14	111.56 (10)	C4—C5—H5	125.00
C3—C4—C5	107.20 (9)	C6—C5—H5	125.00
N1—C4—C5	102.09 (9)	C8—C9—H9	120.00
C5—C4—C14	113.07 (9)	C10—C9—H9	120.00
C3—C4—C14	112.87 (9)	C9—C10—H10	120.00
N1—C4—C3	109.43 (9)	C11—C10—H10	120.00
C4—C5—C6	110.17 (10)	C10—C11—H11	120.00
C5—C6—C7	108.54 (9)	C12—C11—H11	120.00
N2—C6—C5	135.95 (11)	C11—C12—H12	120.00
N2—C6—C7	115.49 (10)	C13—C12—H12	120.00
O3—C7—N1	126.32 (11)	C8—C13—H13	120.00
O3—C7—C6	126.75 (10)	C12—C13—H13	120.00
N1—C7—C6	106.93 (10)	C4—C14—H14A	109.00
N1—C8—C9	118.96 (11)	C4—C14—H14B	109.00
C9—C8—C13	120.50 (11)	C4—C14—H14C	109.00
N1—C8—C13	120.48 (10)	H14A—C14—H14B	110.00
C8—C9—C10	119.68 (12)	H14A—C14—H14C	109.00
C9—C10—C11	120.31 (12)	H14B—C14—H14C	109.00
C10—C11—C12	119.85 (13)	C15—C16—H16	120.00
C11—C12—C13	120.27 (12)	C17—C16—H16	120.00
C8—C13—C12	119.38 (11)	C16—C17—H17	120.00
N2—C15—C16	117.97 (11)	C18—C17—H17	120.00
C16—C15—C20	119.22 (11)	C17—C18—H18	121.00
N2—C15—C20	122.73 (10)	C19—C18—H18	121.00
C15—C16—C17	120.08 (12)	C18—C19—H19	119.00
C16—C17—C18	120.79 (11)	C20—C19—H19	119.00
C17—C18—C19	118.93 (12)	C15—C20—H20	120.00
C18—C19—C20	121.14 (12)	C19—C20—H20	120.00
C15—C20—C19	119.84 (11)
C3—O1—C2—C1	163.94 (11)	O2—C3—C4—N1	−25.34 (16)
C2—O1—C3—O2	2.26 (18)	C3—C4—C5—C6	−113.96 (11)
C2—O1—C3—C4	−179.93 (10)	C14—C4—C5—C6	121.00 (11)
C7—N1—C8—C13	101.78 (13)	N1—C4—C5—C6	1.02 (12)
C7—N1—C4—C5	0.49 (12)	C4—C5—C6—N2	176.18 (12)
C8—N1—C4—C5	−176.44 (10)	C4—C5—C6—C7	−2.01 (13)
C7—N1—C4—C14	−120.55 (10)	C5—C6—C7—O3	−177.72 (11)
C8—N1—C4—C14	62.53 (13)	N2—C6—C7—N1	−176.31 (9)
C4—N1—C8—C9	101.29 (14)	C5—C6—C7—N1	2.30 (12)
C7—N1—C4—C3	113.83 (10)	N2—C6—C7—O3	3.68 (17)
C8—N1—C4—C3	−63.10 (13)	N1—C8—C9—C10	176.91 (12)
C4—N1—C7—C6	−1.65 (12)	C9—C8—C13—C12	0.19 (18)
C4—N1—C7—O3	178.36 (11)	C13—C8—C9—C10	−0.23 (19)
C8—N1—C7—O3	−4.58 (18)	N1—C8—C13—C12	−176.91 (11)
C4—N1—C8—C13	−81.57 (14)	C8—C9—C10—C11	0.1 (2)
C8—N1—C7—C6	175.41 (9)	C9—C10—C11—C12	0.1 (2)
C7—N1—C8—C9	−75.36 (15)	C10—C11—C12—C13	−0.12 (19)
C15—N2—C6—C7	179.61 (10)	C11—C12—C13—C8	−0.02 (19)
C6—N2—C15—C16	−158.37 (11)	N2—C15—C16—C17	−176.86 (11)
C15—N2—C6—C5	1.5 (2)	C20—C15—C16—C17	−0.13 (18)
C6—N2—C15—C20	25.02 (18)	N2—C15—C20—C19	176.70 (11)
O1—C3—C4—C5	−93.17 (11)	C16—C15—C20—C19	0.13 (17)
O1—C3—C4—N1	156.85 (9)	C15—C16—C17—C18	0.00 (19)
O2—C3—C4—C14	−150.20 (12)	C16—C17—C18—C19	0.1 (2)
O1—C3—C4—C14	31.99 (13)	C17—C18—C19—C20	−0.1 (2)
O2—C3—C4—C5	84.64 (14)	C18—C19—C20—C15	0.00 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.898 (17)	2.443 (16)	2.8247 (14)	105.9 (12)
N2—H2N···O3i	0.898 (17)	2.033 (17)	2.9135 (14)	166.3 (14)
C1—H1B···Cg2ii	0.98	2.91	3.6177 (15)	130
C12—H12···Cg3iii	0.95	2.84	3.4865 (14)	126

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C8–C13 and C15–C20 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	0.898 (17)	2.443 (16)	2.8247 (14)	105.9 (12)
N2—H2N⋯O3i	0.898 (17)	2.033 (17)	2.9135 (14)	166.3 (14)
C1—H1B⋯Cg2ii	0.98	2.91	3.6177 (15)	130
C12—H12⋯Cg3iii	0.95	2.84	3.4865 (14)	126

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