7a-Phenyl­tetra­hydro­pyrrolo­[2,1-b]oxazol-5(6H)-one

Linkova, E.I.; Grinev, V.S.; Mayorova, O.A.; Yegorova, A.Y.

doi:10.1107/S2414314620009190

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 7| July 2020| x200919

https://doi.org/10.1107/S2414314620009190

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7a-Phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one

Elena I. Linkova,^a Vyacheslav S. Grinev,^b,^a ^* Oksana A. Mayorova ^b and Alevtina Yu. Yegorova ^a

^aInstitute of Chemistry, N.G. Chernyshevsky National Research Saratov State University, Ulitsa Astrakhanskaya, 83, Saratov 410012, Russian Federation, and ^bInstitute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russian Federation
^*Correspondence e-mail: grinev@ibppm.ru

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 30 June 2020; accepted 6 July 2020; online 10 July 2020)

In the title compound, C₁₂H₁₃NO₂, the pyrrolidinone moiety is almost flat while the oxazole ring adopts an envelope conformation with the carbon atom bearing the phenyl substituent as the flap: the angle between the mean planes of the fused heterocyclic rings is 45.47 (19)°. In the crystal, C—H⋯O and C—H⋯π contacts link the molecules into infinite [010] chains.

Keywords: crystal structure; pyrrolo[2,1-b]oxazol-5(6H)-one; C—H⋯O contacts; C—H⋯π contacts.

CCDC reference: 2014300

Structure description

The title compound, C₁₂H₁₃NO₂, has been reported in the literature several times (Aeberli & Houlihan, 1969 ; Aeberli et al., 1976 ; Amal'chieva & Egorova, 2006 ). It has been also reported for its anti-depressant (Aeberli et al., 1976) and anti-convulsant activities (Trapani et al., 1996 ) as well as the synthetic potential to obtain 4,5-dihydro-2H-pyridazin-3-ones (Lim et al., 2003 ). We now describe its crystal structure.

Molecules of title compound consist of pyrrolidinone and oxazole rings fused via the C3—N1 edge into a bicyclic system (Fig. 1). The pyrrolidinone moiety is almost flat (r.m.s. deviation = 0.054 Å) with a maximum torsion angle N1—C6—C5—C4 of 13.4 (5)°, whereas the minimum torsion angle C5—C4—C3—N1 is 2.7 (5)°. The oxazole ring is more twisted and adopts an envelope conformation with atom C3 as the flap and a maximum torsion angle C2—O1—C3—N1 of −35.7 (4)°. The heterocyclic rings are fused with a dihedral angle between their mean planes of 45.47 (19)°. The phenyl substituent is located orthogonally to the mean plane of the whole bicycle [dihedral angle = 89.28 (14)°].

Figure 1
The molecular structure of the title compound showing 50% displacement ellipsoids.

In contrast to closely related pyrrolopyrimidinones (Grinev et al., 2020 ), there is no classical hydrogen bonding in the crystal of the title molecule, obviously due to the absence of NH groups (Fig. 2). The molecules are connected via weak C5—H5A⋯O2 links (Table 1) to generate infinite chains directed along [010]. The H5A⋯O2 distance of 2.58 Å is significantly longer than the corresponding distance in pyrrolopyrimidinones [2.28 (5)–2.306 (18) Å]. Moreover, there are C10—H10⋯π contacts to an adjacent phenyl ring (Fig. 3), which reinforce the [010] chains.

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2ⁱ	0.97	2.58	3.346 (6)	136
C10—H10⋯Cg3ⁱⁱ	0.93	2.88	3.734 (6)	154
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Figure 2
The packing of the title compound viewed down [100] showing hydrogen bonds as red dashed lines.

Figure 3
The packing of the title compound showing C—H⋯π interactions.

Synthesis and crystallization

5-Phenylfuran-2(3H)-one (1 g, 6 mmol) and ethanolamine (0.34 g, 6 mmol) were placed in a round-bottomed flask equipped with Dean–Stark apparatus. Dry benzene (30 ml) was added and the reaction mixture refluxed for 3–4 h. After being left to stand overnight, the separated crystals and precipitate were washed with benzene and acetone and the solid placed in a vacuum desiccator for drying (yield 0.91 g, 75%; m.p. 65–67°C). The single crystal used for data collection was obtained directly from the cooled reaction mixture.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₃NO₂
M_r	203.23
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	5.7173 (17), 7.346 (3), 12.436 (4)
β (°)	93.07 (3)
V (Å³)	521.5 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.55 × 0.1 × 0.08

Data collection
Diffractometer	Agilent Technologies New Xcalibur, Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.217, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5059, 2406, 1462
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.691

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.160, 1.06
No. of reflections	2406
No. of parameters	137
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2014300

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620009190/hb4353sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620009190/hb4353Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620009190/hb4353Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

7a-Phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one top

Crystal data top

C₁₂H₁₃NO₂	F(000) = 216
M_r = 203.23	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.7173 (17) Å	Cell parameters from 1357 reflections
b = 7.346 (3) Å	θ = 3.5–22.6°
c = 12.436 (4) Å	µ = 0.09 mm⁻¹
β = 93.07 (3)°	T = 295 K
V = 521.5 (3) Å³	Needle, clear colourless
Z = 2	0.55 × 0.1 × 0.08 mm

Data collection top

Agilent Technologies New Xcalibur, Ruby diffractometer	2406 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1462 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 10.4752 pixels mm^-1	θ_max = 29.4°, θ_min = 3.2°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	k = −9→9
T_min = 0.217, T_max = 1.000	l = −16→11
5059 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.0638P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.160	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.16 e Å⁻³
2406 reflections	Δρ_min = −0.15 e Å⁻³
137 parameters	Extinction correction: SHELXL2018/1 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.094 (18)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	U_iso*/U_eq
C1	0.4191 (7)	0.8471 (7)	0.1967 (3)	0.0669 (12)
H1A	0.440537	0.941850	0.143766	0.080*
H1B	0.563590	0.831027	0.240152	0.080*
N1	0.3418 (5)	0.6763 (5)	0.1455 (2)	0.0560 (9)
O1	0.0340 (4)	0.7581 (5)	0.2424 (2)	0.0666 (9)
C2	0.2140 (7)	0.8897 (6)	0.2663 (3)	0.0694 (13)
H2A	0.264333	0.883883	0.341924	0.083*
H2B	0.155301	1.011334	0.250689	0.083*
O2	0.4289 (5)	0.7275 (5)	−0.0288 (2)	0.0743 (10)
C3	0.1537 (6)	0.6008 (6)	0.2049 (3)	0.0545 (10)
C4	−0.0033 (7)	0.4983 (8)	0.1217 (3)	0.0750 (13)
H4A	−0.017904	0.371365	0.141669	0.090*
H4B	−0.158290	0.552282	0.115247	0.090*
C5	0.1181 (7)	0.5165 (7)	0.0181 (3)	0.0686 (12)
H5A	0.180468	0.399755	−0.003026	0.082*
H5B	0.009114	0.559003	−0.038927	0.082*
C6	0.3109 (7)	0.6501 (6)	0.0374 (3)	0.0559 (10)
C7	0.2432 (6)	0.4828 (5)	0.2990 (3)	0.0489 (9)
C8	0.4440 (6)	0.3789 (6)	0.2926 (3)	0.0622 (11)
H8	0.529967	0.384189	0.231306	0.075*
C9	0.5168 (7)	0.2675 (6)	0.3775 (4)	0.0712 (12)
H9	0.653085	0.199387	0.373066	0.085*
C10	0.3912 (8)	0.2559 (7)	0.4680 (4)	0.0724 (12)
H10	0.441108	0.179917	0.524518	0.087*
C11	0.1929 (9)	0.3565 (8)	0.4745 (3)	0.0746 (13)
H11	0.107507	0.349304	0.535934	0.090*
C12	0.1163 (7)	0.4699 (6)	0.3904 (3)	0.0633 (11)
H12	−0.020343	0.537312	0.395607	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.068 (2)	0.072 (3)	0.061 (3)	−0.019 (3)	0.005 (2)	−0.004 (2)
N1	0.0587 (17)	0.066 (2)	0.0439 (19)	−0.0115 (16)	0.0075 (13)	0.0058 (16)
O1	0.0574 (14)	0.0675 (18)	0.076 (2)	0.0055 (15)	0.0118 (13)	0.0046 (16)
C2	0.075 (3)	0.063 (3)	0.070 (3)	−0.005 (2)	0.005 (2)	0.000 (2)
O2	0.090 (2)	0.082 (2)	0.0525 (18)	−0.0011 (18)	0.0205 (15)	0.0124 (16)
C3	0.0511 (19)	0.063 (2)	0.050 (2)	−0.0077 (18)	0.0097 (16)	0.001 (2)
C4	0.075 (3)	0.088 (4)	0.061 (3)	−0.026 (3)	−0.002 (2)	0.003 (3)
C5	0.078 (2)	0.068 (3)	0.060 (2)	−0.003 (2)	0.006 (2)	−0.012 (2)
C6	0.061 (2)	0.060 (3)	0.047 (2)	0.008 (2)	0.0061 (16)	0.005 (2)
C7	0.0494 (19)	0.051 (2)	0.047 (2)	−0.0065 (17)	0.0098 (14)	0.0002 (19)
C8	0.060 (2)	0.073 (3)	0.055 (2)	−0.001 (2)	0.0119 (18)	0.006 (2)
C9	0.064 (2)	0.068 (3)	0.082 (3)	0.005 (2)	0.007 (2)	0.012 (3)
C10	0.098 (3)	0.062 (3)	0.057 (3)	−0.011 (3)	−0.002 (2)	0.013 (2)
C11	0.106 (3)	0.069 (3)	0.052 (2)	−0.003 (3)	0.028 (2)	0.009 (2)
C12	0.070 (2)	0.062 (3)	0.059 (2)	−0.003 (2)	0.0219 (18)	0.002 (2)

Geometric parameters (Å, º) top

C1—H1A	0.9700	C4—C5	1.502 (6)
C1—H1B	0.9700	C5—H5A	0.9700
C1—N1	1.464 (6)	C5—H5B	0.9700
C1—C2	1.527 (6)	C5—C6	1.486 (6)
N1—C3	1.447 (5)	C7—C8	1.384 (5)
N1—C6	1.361 (5)	C7—C12	1.385 (5)
O1—C2	1.432 (5)	C8—H8	0.9300
O1—C3	1.434 (5)	C8—C9	1.382 (6)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C9—C10	1.370 (6)
O2—C6	1.230 (5)	C10—H10	0.9300
C3—C4	1.531 (5)	C10—C11	1.359 (7)
C3—C7	1.523 (5)	C11—H11	0.9300
C4—H4A	0.9700	C11—C12	1.389 (6)
C4—H4B	0.9700	C12—H12	0.9300

H1A—C1—H1B	109.3	C4—C5—H5A	110.3
N1—C1—H1A	111.5	C4—C5—H5B	110.3
N1—C1—H1B	111.5	H5A—C5—H5B	108.6
N1—C1—C2	101.5 (3)	C6—C5—C4	107.0 (4)
C2—C1—H1A	111.5	C6—C5—H5A	110.3
C2—C1—H1B	111.5	C6—C5—H5B	110.3
C3—N1—C1	108.8 (3)	N1—C6—C5	108.0 (4)
C6—N1—C1	124.8 (4)	O2—C6—N1	123.3 (4)
C6—N1—C3	112.9 (3)	O2—C6—C5	128.7 (4)
C2—O1—C3	105.2 (3)	C8—C7—C3	121.1 (3)
C1—C2—H2A	110.1	C8—C7—C12	118.8 (4)
C1—C2—H2B	110.1	C12—C7—C3	120.0 (3)
O1—C2—C1	108.0 (3)	C7—C8—H8	120.0
O1—C2—H2A	110.1	C9—C8—C7	120.0 (4)
O1—C2—H2B	110.1	C9—C8—H8	120.0
H2A—C2—H2B	108.4	C8—C9—H9	119.5
N1—C3—C4	105.6 (3)	C10—C9—C8	121.0 (4)
N1—C3—C7	112.5 (3)	C10—C9—H9	119.5
O1—C3—N1	103.8 (3)	C9—C10—H10	120.3
O1—C3—C4	110.1 (3)	C11—C10—C9	119.4 (4)
O1—C3—C7	110.8 (3)	C11—C10—H10	120.3
C7—C3—C4	113.6 (4)	C10—C11—H11	119.6
C3—C4—H4A	110.8	C10—C11—C12	120.8 (4)
C3—C4—H4B	110.8	C12—C11—H11	119.6
H4A—C4—H4B	108.9	C7—C12—C11	120.1 (4)
C5—C4—C3	104.8 (3)	C7—C12—H12	120.0
C5—C4—H4A	110.8	C11—C12—H12	120.0
C5—C4—H4B	110.8

C1—N1—C3—O1	33.1 (3)	C3—O1—C2—C1	25.9 (4)
C1—N1—C3—C4	148.9 (4)	C3—C4—C5—C6	−9.5 (5)
C1—N1—C3—C7	−86.7 (4)	C3—C7—C8—C9	−177.5 (4)
C1—N1—C6—O2	32.0 (6)	C3—C7—C12—C11	177.4 (4)
C1—N1—C6—C5	−148.2 (4)	C4—C3—C7—C8	85.8 (4)
N1—C1—C2—O1	−5.7 (4)	C4—C3—C7—C12	−90.5 (4)
N1—C3—C4—C5	2.7 (5)	C4—C5—C6—N1	13.4 (5)
N1—C3—C7—C8	−34.1 (5)	C4—C5—C6—O2	−166.8 (4)
N1—C3—C7—C12	149.6 (4)	C6—N1—C3—O1	−109.9 (4)
O1—C3—C4—C5	114.1 (4)	C6—N1—C3—C4	5.9 (5)
O1—C3—C7—C8	−149.7 (3)	C6—N1—C3—C7	130.3 (4)
O1—C3—C7—C12	34.0 (5)	C7—C3—C4—C5	−121.0 (4)
C2—C1—N1—C3	−16.7 (4)	C7—C8—C9—C10	0.9 (6)
C2—C1—N1—C6	120.9 (4)	C8—C7—C12—C11	1.0 (6)
C2—O1—C3—N1	−35.7 (4)	C8—C9—C10—C11	−0.4 (7)
C2—O1—C3—C4	−148.3 (3)	C9—C10—C11—C12	0.2 (7)
C2—O1—C3—C7	85.2 (3)	C10—C11—C12—C7	−0.5 (7)
C3—N1—C6—O2	168.1 (4)	C12—C7—C8—C9	−1.1 (5)
C3—N1—C6—C5	−12.2 (5)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2ⁱ	0.97	2.58	3.346 (6)	136
C10—H10···Cg3ⁱⁱ	0.93	2.88	3.734 (6)	154

Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y−1/2, −z+1.

Funding information

Funding for this research was provided by: Russian Foundation for Basic Research (grant No. 19-33-90157 to Alevtina Yu. Yegorova).

References

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

7a-Phenyl­tetra­hydro­pyrrolo­[2,1-b]oxazol-5(6H)-one

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds

7a-Phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one