3-Benzamido-1-benzoyl-1H-pyrrol-2(5H)-one

Kasunič, M.; Verček, B.; Mušič, I.; Golobič, A.

doi:10.1107/S1600536810006483

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o687

doi:10.1107/S1600536810006483

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3-Benzamido-1-benzoyl-1H-pyrrol-2(5H)-one

Marta Kasunič,^a ^* Bojan Verček,^a Irena Mušič ^a and Amalija Golobič ^a

^aFaculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
^*Correspondence e-mail: marta.kasunic@fkkt.uni-lj.si

(Received 18 February 2010; accepted 19 February 2010; online 24 February 2010)

In the title compound, C₁₈H₁₄N₂O₃, one of the phenyl rings is almost coplanar with the pyrrole ring [dihedral angle = 2.56 (14)°], whereas the other one is tilted by 63.01 (6)° with respect to the pyrrole ring. Since the NH group is shielded from possible acceptors, this group is not involved in hydrogen bonding.

Related literature

For the synthesis of 1,5-dihydro-2H-pyrrol-2-ones, see: Gao et al. (1997 ); Alizadeh et al. (2006 ); Nedolya et al. (2002 ); Mušič et al. (1998 ).

Experimental

Crystal data

C₁₈H₁₄N₂O₃
M_r = 306.31
Monoclinic, P 2₁ /c
a = 20.966 (2) Å
b = 5.8891 (7) Å
c = 12.329 (1) Å
β = 95.908 (8)°
V = 1514.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.58 × 0.36 × 0.09 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
13450 measured reflections
3648 independent reflections
2119 reflections with I > 2σ(I)
R_int = 0.056
3 standard reflections every 333.3 min intensity decay: 1.1%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.132
S = 1.00
3648 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: the XRAY76 System (Stewart et al., 1976 ); data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006483/bt5197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006483/bt5197Isup2.hkl

checkCIF report

Comment top

1,5-dihydro-2H-pyrrol-2-ones comprise a family of lactams which are found as substructures in several natural products with promising pharmalogical properties. Several reports on synthesis of substituted 1,5-dihydro-2H-pyrrol-2-ones exist and these compounds can be prepared via different synthetic pathways (e.g. Gao et al., 1997; Alizadeh et al., 2006; Nedolya et al., 2002), Mušič et al. (1998). The asymmetry unit of the title compound with atom labelling scheme can be seen in Fig. 1.

Related literature top

For the synthesis of 1,5-dihydro-2H-pyrrol-2-ones, see: Gao et al. (1997); Alizadeh et al. (2006); Nedolya et al. (2002); Mušič et al. (1998).

Experimental top

The title compound was prepared according to the procedure by Mušič et al. (1998). The crystals, suitable for X-ray structure analysis, were obtained by slow crystallization from the mixture of acetonitrile and hexane at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: the XRAY76 System (Stewart et al., 1976); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELX97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELX97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are drawn as small spheres of arbitrary radii.

3-Benzamido-1-benzoyl-1H-pyrrol-2(5H)-one top

Crystal data top

C₁₈H₁₄N₂O₃	F(000) = 640
M_r = 306.31	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 75 reflections
a = 20.966 (2) Å	θ = 8.0–15.3°
b = 5.8891 (7) Å	µ = 0.09 mm⁻¹
c = 12.329 (1) Å	T = 293 K
β = 95.908 (8)°	Plate, pale yellow
V = 1514.2 (3) Å³	0.58 × 0.36 × 0.09 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.056
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 2.0°
Graphite monochromator	h = −27→27
ω/2θ scans [width (0.85 + 0.3tanθ)]	k = −7→7
13450 measured reflections	l = −16→14
3648 independent reflections	3 standard reflections every 333.3 min
2119 reflections with I > 2σ(I)	intensity decay: 1.1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0676P)² + 0.1617P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3648 reflections	Δρ_max = 0.16 e Å⁻³
209 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELX97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (3)

Crystal data top

C₁₈H₁₄N₂O₃	V = 1514.2 (3) Å³
M_r = 306.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.966 (2) Å	µ = 0.09 mm⁻¹
b = 5.8891 (7) Å	T = 293 K
c = 12.329 (1) Å	0.58 × 0.36 × 0.09 mm
β = 95.908 (8)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.056
13450 measured reflections	3 standard reflections every 333.3 min
3648 independent reflections	intensity decay: 1.1%
2119 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
3648 reflections	Δρ_min = −0.18 e Å⁻³
209 parameters

Special details top

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 > 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.

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

	x	y	z	U_iso*/U_eq
N1	0.80491 (6)	0.1771 (2)	0.90089 (10)	0.0492 (3)
N2	0.69375 (7)	0.6347 (2)	0.88815 (11)	0.0554 (4)
H2	0.6985	0.6820	0.8235	0.066*
O1	0.77372 (6)	0.4192 (2)	0.75402 (9)	0.0632 (4)
O2	0.85617 (8)	−0.1579 (2)	0.90309 (12)	0.0846 (5)
O3	0.64221 (7)	0.6962 (3)	1.03607 (10)	0.0784 (4)
C1	0.78338 (8)	0.1439 (3)	1.00943 (12)	0.0534 (4)
H1A	0.8190	0.1548	1.0660	0.064*
H1B	0.7627	−0.0024	1.0147	0.064*
C2	0.73736 (8)	0.3319 (3)	1.01751 (13)	0.0550 (4)
H2A	0.7162	0.3627	1.0785	0.066*
C3	0.73060 (7)	0.4501 (3)	0.92579 (12)	0.0483 (4)
C4	0.77164 (7)	0.3562 (3)	0.84693 (12)	0.0472 (4)
C5	0.84667 (8)	0.0250 (3)	0.85911 (13)	0.0534 (4)
C6	0.88045 (7)	0.0966 (3)	0.76467 (12)	0.0453 (4)
C7	0.88460 (8)	−0.0552 (3)	0.67966 (14)	0.0549 (4)
H7	0.8640	−0.1950	0.6800	0.066*
C8	0.91946 (9)	0.0018 (3)	0.59465 (14)	0.0634 (5)
H8	0.9210	−0.0975	0.5363	0.076*
C9	0.95206 (9)	0.2049 (3)	0.59581 (15)	0.0619 (5)
H9	0.9763	0.2408	0.5391	0.074*
C10	0.94882 (8)	0.3549 (3)	0.68073 (14)	0.0555 (4)
H10	0.9712	0.4913	0.6817	0.067*
C11	0.91240 (7)	0.3029 (3)	0.76453 (12)	0.0487 (4)
H11	0.9093	0.4061	0.8208	0.058*
C12	0.65088 (8)	0.7482 (3)	0.94360 (13)	0.0528 (4)
C13	0.61696 (8)	0.9416 (3)	0.88463 (13)	0.0512 (4)
C14	0.57527 (10)	1.0680 (4)	0.93989 (16)	0.0712 (6)
H14	0.5678	1.0268	1.0103	0.085*
C15	0.54448 (12)	1.2550 (4)	0.8915 (2)	0.0884 (7)
H15	0.5166	1.3397	0.9294	0.106*
C16	0.55488 (11)	1.3153 (4)	0.7884 (2)	0.0860 (7)
H16	0.5347	1.4425	0.7561	0.103*
C17	0.59485 (12)	1.1893 (5)	0.7325 (2)	0.0956 (8)
H17	0.6015	1.2299	0.6616	0.115*
C18	0.62549 (10)	1.0025 (4)	0.77981 (16)	0.0770 (6)
H18	0.6523	0.9165	0.7403	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0550 (8)	0.0540 (8)	0.0394 (7)	0.0026 (7)	0.0086 (6)	0.0046 (6)
N2	0.0570 (8)	0.0713 (10)	0.0406 (7)	0.0103 (7)	0.0184 (6)	0.0029 (7)
O1	0.0735 (8)	0.0808 (9)	0.0375 (6)	0.0250 (7)	0.0167 (5)	0.0084 (6)
O2	0.1141 (12)	0.0581 (8)	0.0851 (10)	0.0181 (8)	0.0264 (9)	0.0236 (7)
O3	0.0878 (10)	0.1034 (11)	0.0492 (7)	0.0198 (8)	0.0315 (7)	0.0071 (7)
C1	0.0575 (10)	0.0645 (11)	0.0387 (8)	−0.0111 (8)	0.0071 (7)	0.0064 (8)
C2	0.0519 (9)	0.0741 (11)	0.0409 (8)	−0.0055 (9)	0.0139 (7)	0.0004 (8)
C3	0.0457 (8)	0.0620 (11)	0.0385 (8)	−0.0033 (8)	0.0105 (6)	−0.0017 (7)
C4	0.0489 (9)	0.0573 (10)	0.0361 (8)	0.0018 (8)	0.0075 (6)	−0.0009 (7)
C5	0.0589 (10)	0.0492 (10)	0.0515 (9)	0.0025 (8)	0.0031 (8)	0.0027 (8)
C6	0.0466 (8)	0.0432 (8)	0.0457 (8)	0.0093 (7)	0.0027 (6)	−0.0018 (7)
C7	0.0574 (10)	0.0444 (9)	0.0625 (11)	0.0076 (8)	0.0048 (8)	−0.0092 (8)
C8	0.0682 (12)	0.0659 (12)	0.0566 (11)	0.0189 (10)	0.0093 (9)	−0.0179 (9)
C9	0.0539 (10)	0.0758 (13)	0.0584 (11)	0.0125 (9)	0.0168 (8)	0.0003 (9)
C10	0.0486 (9)	0.0561 (10)	0.0624 (10)	−0.0002 (8)	0.0089 (8)	0.0008 (8)
C11	0.0514 (9)	0.0466 (9)	0.0475 (9)	0.0047 (7)	0.0026 (7)	−0.0060 (7)
C12	0.0484 (9)	0.0688 (11)	0.0432 (9)	−0.0040 (8)	0.0152 (7)	−0.0079 (8)
C13	0.0446 (8)	0.0621 (10)	0.0479 (9)	−0.0041 (8)	0.0098 (7)	−0.0112 (8)
C14	0.0744 (13)	0.0822 (14)	0.0590 (11)	0.0110 (11)	0.0160 (9)	−0.0205 (10)
C15	0.0897 (17)	0.0788 (15)	0.0968 (17)	0.0231 (13)	0.0096 (13)	−0.0297 (13)
C16	0.0808 (16)	0.0710 (14)	0.1039 (19)	0.0063 (12)	−0.0011 (13)	0.0066 (13)
C17	0.0862 (16)	0.116 (2)	0.0873 (16)	0.0289 (15)	0.0238 (13)	0.0341 (15)
C18	0.0704 (12)	0.1031 (16)	0.0608 (11)	0.0271 (12)	0.0233 (10)	0.0130 (11)

Geometric parameters (Å, º) top

N1—C5	1.388 (2)	C8—C9	1.377 (3)
N1—C4	1.395 (2)	C8—H8	0.9300
N1—C1	1.4687 (19)	C9—C10	1.377 (2)
N2—C12	1.360 (2)	C9—H9	0.9300
N2—C3	1.385 (2)	C10—C11	1.381 (2)
N2—H2	0.8600	C10—H10	0.9300
O1—C4	1.2091 (18)	C11—H11	0.9300
O2—C5	1.213 (2)	C12—C13	1.492 (2)
O3—C12	1.2121 (19)	C13—C18	1.370 (2)
C1—C2	1.479 (3)	C13—C14	1.380 (2)
C1—H1A	0.9700	C14—C15	1.381 (3)
C1—H1B	0.9700	C14—H14	0.9300
C2—C3	1.323 (2)	C15—C16	1.358 (3)
C2—H2A	0.9300	C15—H15	0.9300
C3—C4	1.471 (2)	C16—C17	1.359 (3)
C5—C6	1.485 (2)	C16—H16	0.9300
C6—C11	1.387 (2)	C17—C18	1.373 (3)
C6—C7	1.387 (2)	C17—H17	0.9300
C7—C8	1.379 (2)	C18—H18	0.9300
C7—H7	0.9300

C5—N1—C4	127.91 (13)	C7—C8—H8	119.8
C5—N1—C1	121.13 (13)	C8—C9—C10	120.13 (17)
C4—N1—C1	110.46 (13)	C8—C9—H9	119.9
C12—N2—C3	126.31 (14)	C10—C9—H9	119.9
C12—N2—H2	116.8	C9—C10—C11	120.07 (17)
C3—N2—H2	116.8	C9—C10—H10	120.0
N1—C1—C2	103.04 (13)	C11—C10—H10	120.0
N1—C1—H1A	111.2	C10—C11—C6	119.96 (15)
C2—C1—H1A	111.2	C10—C11—H11	120.0
N1—C1—H1B	111.2	C6—C11—H11	120.0
C2—C1—H1B	111.2	O3—C12—N2	121.29 (17)
H1A—C1—H1B	109.1	O3—C12—C13	122.77 (15)
C3—C2—C1	110.47 (14)	N2—C12—C13	115.92 (14)
C3—C2—H2A	124.8	C18—C13—C14	118.38 (18)
C1—C2—H2A	124.8	C18—C13—C12	123.87 (16)
C2—C3—N2	134.92 (15)	C14—C13—C12	117.74 (16)
C2—C3—C4	110.40 (15)	C15—C14—C13	120.6 (2)
N2—C3—C4	114.67 (13)	C15—C14—H14	119.7
O1—C4—N1	128.21 (15)	C13—C14—H14	119.7
O1—C4—C3	126.27 (15)	C16—C15—C14	120.0 (2)
N1—C4—C3	105.48 (13)	C16—C15—H15	120.0
O2—C5—N1	119.19 (16)	C14—C15—H15	120.0
O2—C5—C6	122.21 (16)	C15—C16—C17	119.9 (2)
N1—C5—C6	118.54 (14)	C15—C16—H16	120.0
C11—C6—C7	119.70 (15)	C17—C16—H16	120.0
C11—C6—C5	121.26 (14)	C16—C17—C18	120.5 (2)
C7—C6—C5	118.79 (15)	C16—C17—H17	119.7
C8—C7—C6	119.78 (17)	C18—C17—H17	119.7
C8—C7—H7	120.1	C13—C18—C17	120.6 (2)
C6—C7—H7	120.1	C13—C18—H18	119.7
C9—C8—C7	120.31 (16)	C17—C18—H18	119.7
C9—C8—H8	119.8

C5—N1—C1—C2	−176.46 (15)	C11—C6—C7—C8	−1.2 (2)
C4—N1—C1—C2	−3.92 (17)	C5—C6—C7—C8	−175.60 (15)
N1—C1—C2—C3	2.68 (19)	C6—C7—C8—C9	2.4 (3)
C1—C2—C3—N2	178.14 (18)	C7—C8—C9—C10	−1.5 (3)
C1—C2—C3—C4	−0.6 (2)	C8—C9—C10—C11	−0.6 (3)
C12—N2—C3—C2	−0.5 (3)	C9—C10—C11—C6	1.8 (2)
C12—N2—C3—C4	178.20 (15)	C7—C6—C11—C10	−0.9 (2)
C5—N1—C4—O1	−2.2 (3)	C5—C6—C11—C10	173.38 (15)
C1—N1—C4—O1	−174.11 (17)	C3—N2—C12—O3	1.6 (3)
C5—N1—C4—C3	175.56 (15)	C3—N2—C12—C13	−179.80 (15)
C1—N1—C4—C3	3.67 (17)	O3—C12—C13—C18	−179.38 (19)
C2—C3—C4—O1	175.90 (17)	N2—C12—C13—C18	2.0 (3)
N2—C3—C4—O1	−3.1 (3)	O3—C12—C13—C14	1.6 (3)
C2—C3—C4—N1	−1.93 (19)	N2—C12—C13—C14	−177.04 (16)
N2—C3—C4—N1	179.08 (13)	C18—C13—C14—C15	−1.9 (3)
C4—N1—C5—O2	−157.39 (17)	C12—C13—C14—C15	177.23 (18)
C1—N1—C5—O2	13.7 (2)	C13—C14—C15—C16	0.4 (3)
C4—N1—C5—C6	25.3 (2)	C14—C15—C16—C17	1.0 (4)
C1—N1—C5—C6	−163.60 (14)	C15—C16—C17—C18	−0.7 (4)
O2—C5—C6—C11	−127.91 (19)	C14—C13—C18—C17	2.1 (3)
N1—C5—C6—C11	49.3 (2)	C12—C13—C18—C17	−176.9 (2)
O2—C5—C6—C7	46.4 (2)	C16—C17—C18—C13	−0.9 (4)
N1—C5—C6—C7	−136.36 (16)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₃
M_r	306.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	20.966 (2), 5.8891 (7), 12.329 (1)
β (°)	95.908 (8)
V (Å³)	1514.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.58 × 0.36 × 0.09

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13450, 3648, 2119
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.00
No. of reflections	3648
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), the XRAY76 System (Stewart et al., 1976), XCAD4 (Harms & Wocadlo, 1995), SIR92 (Altomare et al., 1993), SHELX97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Acknowledgements

This work was supported by the Ministry of Higher Education, Science and Technology of the Republic of Slovenia (grants P1–0175 and MR-29397).

References

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